DD291324A5 - Verfahren zur herstellung von 2,4-diamino-6-piperidinyl-pyrimidin-3-n-oxid - Google Patents

Verfahren zur herstellung von 2,4-diamino-6-piperidinyl-pyrimidin-3-n-oxid Download PDF

Info

Publication number: DD291324A5
Authority: DD; German Democratic Republic
Prior art keywords: oxide; diamino; mol; hydroxylamine; methanol
Prior art date: 1989-01-04

Application number

DD90336935A

Other languages

German (de)

English (en)

Inventor

Lester Mills

Hans P Mettler

Felix Previdoli

Francois Moulin

Original Assignee

��@��k��

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.)

1989-01-04

Filing date

1990-01-04

Publication date

1991-06-27

1990-01-04 Application filed by ��@��k�� filed Critical ��@��k��

1991-06-27 Publication of DD291324A5 publication Critical patent/DD291324A5/de

Links

238000004519 manufacturing process Methods 0.000 title abstract description 3
238000000034 method Methods 0.000 claims abstract description 21
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims abstract description 11
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
-1 alkali metal alkoxide Chemical class 0.000 claims description 8
WFBHRSAKANVBKH-UHFFFAOYSA-N N-hydroxyguanidine Chemical compound NC(=N)NO WFBHRSAKANVBKH-UHFFFAOYSA-N 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
150000001204 N-oxides Chemical class 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
238000005660 chlorination reaction Methods 0.000 claims description 4
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 2
MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 2
239000002253 acid Substances 0.000 claims 2
150000001340 alkali metals Chemical class 0.000 claims 1
150000003512 tertiary amines Chemical class 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
229960003632 minoxidil Drugs 0.000 description 6
238000010992 reflux Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
FUQFHOLPJJETAP-UHFFFAOYSA-N carbamimidoyl chloride;hydron;chloride Chemical compound Cl.NC(Cl)=N FUQFHOLPJJETAP-UHFFFAOYSA-N 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
ZIMGGGWCDYVHOY-UHFFFAOYSA-N 3-hydroxy-2-imino-6-(1-piperidinyl)-4-pyrimidinamine Chemical compound N=C1N(O)C(N)=CC(N2CCCCC2)=N1 ZIMGGGWCDYVHOY-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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 2
WCBQLGUHDSVCJW-UHFFFAOYSA-N O.NC1=CC(O)=NC(N)=[N+]1[O-] Chemical compound O.NC1=CC(O)=NC(N)=[N+]1[O-] WCBQLGUHDSVCJW-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
QJIUMVUZDYPQRT-UHFFFAOYSA-N 6-chloro-2,4-pyrimidinediamine Chemical compound NC1=CC(Cl)=NC(N)=N1 QJIUMVUZDYPQRT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
MCPDUKPEJHLEPQ-UHFFFAOYSA-N Cl.NC1=CC(Cl)=NC(N)=[N+]1[O-] Chemical compound Cl.NC1=CC(Cl)=NC(N)=[N+]1[O-] MCPDUKPEJHLEPQ-UHFFFAOYSA-N 0.000 description 1
OZBSINZMPZMBDI-UHFFFAOYSA-N NC1=[N+](C(=CC(=N1)N)Cl)[O-] Chemical compound NC1=[N+](C(=CC(=N1)N)Cl)[O-] OZBSINZMPZMBDI-UHFFFAOYSA-N 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical class CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
230000003779 hair growth Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
OCRCMLMRESQTQR-UHFFFAOYSA-N n,n-dibutylbutan-1-amine;n,n-diethylethanamine Chemical compound CCN(CC)CC.CCCCN(CCCC)CCCC OCRCMLMRESQTQR-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical class NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD90336935A 1989-01-04 1990-01-04 Verfahren zur herstellung von 2,4-diamino-6-piperidinyl-pyrimidin-3-n-oxid DD291324A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH2089		1989-01-04

Publications (1)

Publication Number	Publication Date
DD291324A5 true DD291324A5 (de)	1991-06-27

Family

ID=4177565

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90336935A DD291324A5 (de)	1989-01-04	1990-01-04	Verfahren zur herstellung von 2,4-diamino-6-piperidinyl-pyrimidin-3-n-oxid

Country Status (14)

Country	Link
US (1)	US4959475A (es)
EP (1)	EP0377437B1 (es)
JP (1)	JPH02225474A (es)
AR (1)	AR247208A1 (es)
AT (1)	ATE115139T1 (es)
CA (1)	CA2007047A1 (es)
CZ (1)	CZ5390A3 (es)
DD (1)	DD291324A5 (es)
DE (1)	DE59007890D1 (es)
DK (1)	DK0377437T3 (es)
ES (1)	ES2064491T3 (es)
HU (1)	HU204809B (es)
IL (1)	IL92948A0 (es)
RU (1)	RU1795970C (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2706896B1 (es) *	1993-06-23	1996-04-12	Caillot Jean Luc
FR2879164B1 (fr) *	2004-12-09	2007-02-23	Airbus France Sas	Aeronef super-transporteur
CN110272391B (zh) *	2019-07-03	2022-10-28	天津药物研究院药业有限责任公司	一种米诺地尔的精制方法
CN114965738B (zh) *	2022-04-15	2024-03-29	武汉海特生物创新医药研究有限公司	一种2,4-二氨基-6-羟基嘧啶起始物料纯度的hplc-uv检测方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1915668A1 (de)	1969-03-27	1970-10-08	Sueddeutsche Kalkstickstoff	Verfahren zur Herstellung von Halogenformamidiniumhalogeniden
US3644364A (en) *	1970-03-31	1972-02-22	Upjohn Co	Compounds and process
US3910928A (en) *	1974-04-26	1975-10-07	Upjohn Co	3-(Cyanimino)-propionitriles
HU177601B (en) *	1978-10-27	1981-11-28	Egyt Gyogyszervegyeszeti Gyar	New process for preparing 6-piperidino-2,4-diamino-pyrimidine-3-oxide
CH660589A5 (de) *	1983-01-28	1987-05-15	Lonza Ag	Verfahren zur herstellung von 2-substituierten 5-nitroso-4,6-diamino-pyrimidinen.
HU196067B (en) *	1986-07-10	1988-09-28	Richter Gedeon Vegyeszet	Process for production of 6-amin-1,2-dihydro-1-hydroxi-2-imino-4-piperidin-piramidin
HU196061B (en)	1986-07-10	1988-09-28	Richter Gedeon Vegyeszet	Process for production of pirimidine-derivatives
DE8618514U1 (de) *	1986-07-10	1986-08-28	Alfi Zitzmann GmbH & Co, 6980 Wertheim	Vorrichtung zum Kühlen von Getränkebehältern, insbesondere Flaschen

1989
- 1989-12-28 JP JP1338863A patent/JPH02225474A/ja active Pending
- 1989-12-28 US US07/458,292 patent/US4959475A/en not_active Expired - Fee Related
1990
- 1990-01-01 IL IL92948A patent/IL92948A0/xx not_active IP Right Cessation
- 1990-01-02 DK DK90100029.9T patent/DK0377437T3/da not_active Application Discontinuation
- 1990-01-02 DE DE59007890T patent/DE59007890D1/de not_active Expired - Fee Related
- 1990-01-02 AT AT90100029T patent/ATE115139T1/de not_active IP Right Cessation
- 1990-01-02 ES ES90100029T patent/ES2064491T3/es not_active Expired - Lifetime
- 1990-01-02 EP EP90100029A patent/EP0377437B1/de not_active Expired - Lifetime
- 1990-01-02 AR AR90315858A patent/AR247208A1/es active
- 1990-01-03 CA CA002007047A patent/CA2007047A1/en not_active Abandoned
- 1990-01-03 RU SU904742749A patent/RU1795970C/ru active
- 1990-01-04 HU HU9036A patent/HU204809B/hu not_active IP Right Cessation
- 1990-01-04 CZ CS9053A patent/CZ5390A3/cs unknown
- 1990-01-04 DD DD90336935A patent/DD291324A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
HU900036D0 (en)	1990-03-28
DK0377437T3 (da)	1995-02-06
RU1795970C (ru)	1993-02-15
JPH02225474A (ja)	1990-09-07
CZ5390A3 (en)	1995-07-12
EP0377437A1 (de)	1990-07-11
CA2007047A1 (en)	1990-07-04
AR247208A1 (es)	1994-11-30
US4959475A (en)	1990-09-25
IL92948A0 (en)	1990-09-17
ATE115139T1 (de)	1994-12-15
DE59007890D1 (de)	1995-01-19
HUT53898A (en)	1990-12-28
HU204809B (en)	1992-02-28
EP0377437B1 (de)	1994-12-07
ES2064491T3 (es)	1995-02-01

Legal Events

Date	Code	Title	Description
1995-08-03	ENJ	Ceased due to non-payment of renewal fee

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DE69516847T2 (de)	2000-10-26	Chlorpyrimidine als zwischenprodukte
EP0816344B1 (de)	2003-06-18	Verfahren zur Herstellung von 2,5-Diamino-4,6-dichlorpyrimidin
EP0122580B1 (de)	1987-10-28	Pyrimidinderivate, deren Herstellung und pharmazeutische Präparate
DE2505297C3 (de)	1979-06-13	Verfahren zur Herstellung von in 2- und 6-Stellung des Phenylkerns substituierten 2-Phenylamino-2-imidazoun-Derivaten
DE69706981T2 (de)	2002-06-06	Verfahren zur herstellung von pyrimidin-derivaten
EP0172515B1 (de)	1987-05-13	Alpha-(o-chlorphenyl)-aminomethylen-beta-formylaminopropionitril, Verfahren zu seiner Herstellung sowie Verwendung zur Herstellung von 2-Methyl-4-amino-5-formylaminomethylpyrimidin
EP1345939A2 (de)	2003-09-24	Verfahren zur herstellung von sulfonamid-substituierten imidazotriazinonen
DD291324A5 (de)	1991-06-27	Verfahren zur herstellung von 2,4-diamino-6-piperidinyl-pyrimidin-3-n-oxid
DE3784795T2 (de)	1993-06-24	Verfahren zur herstellung von 5,6-substituierten-2,4-chinazolindiaminen und zwischenprodukten.
DE60114098T2 (de)	2006-05-18	Ein Verfahren zur Herstellung von Trifluorothymidinderivaten
EP0816345A1 (de)	1998-01-07	Verfahren zur Herstellung von 4,6-Dihydroxypyrimidin
CH638516A5 (en)	1983-09-30	Process for preparing substituted aminoquinazoline derivatives
EP0552758A1 (de)	1993-07-28	N-5-geschützte 2,5-Diamino-4,6-dichlorpyrimidine und Verfahren zu deren Herstellung
DE1720024B2 (de)	1979-04-19	Verfahren zur Herstellung von 3-Amino-4-carboxamidopyrazol
EP0001760B1 (de)	1981-01-07	Alpha-aminomethylen-beta-formylaminopropionitril, Verfahren zu seiner Herstellung sowie Verwendung zur Herstellung von 2-Methyl-4-amino-5-formylaminomethyl-pyrimidin
EP0603893B1 (de)	2001-08-08	Verfahren zur Herstellung von 2-Ethoxy-4,6-dihydroxypyrimidin oder dessen Alkalisalz
DE2715675C2 (es)	1990-12-13
DE4342131A1 (de)	1995-06-14	Neues Verfahren zur Herstellung von 2-Amino-6-chlorpurin
EP0358044B1 (de)	1994-01-26	Verfahren zum Fällen von Cytosin aus alkalischen Lösungen mit Schwefelsäure
DE2065698A1 (de)	1974-12-12	Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon
DE2801248C3 (de)	1979-10-31	Verfahren zur Herstellung von 2-Amino-4-hydroxychinolinen
DE1814082C3 (de)	1979-11-29	Herstellung und ihre Weiterverarbeitung zu Pyrazolopyrimidinen
EP0684243A1 (de)	1995-11-29	Verfahren zur Herstellung von 2-Amino-6-chlorpurin und 2-Acylamino-6-chlorpurinen
CH650006A5 (en)	1985-06-28	Process for the preparation of 5-fluorouracil derivatives
DE2433176A1 (de)	1976-01-22	2-halopyrimidinderivate und verfahren zu ihrer herstellung