SU900812A3 - Способ получени гидрохлорида 6,7-диметокси-4-амино-2-[4-(2-фуроил)-1-пиперазинил-ХИНАЗОЛИНА - Google Patents
Способ получени гидрохлорида 6,7-диметокси-4-амино-2-[4-(2-фуроил)-1-пиперазинил-ХИНАЗОЛИНА Download PDFInfo
- Publication number
- SU900812A3 SU900812A3 SU802874898A SU2874898A SU900812A3 SU 900812 A3 SU900812 A3 SU 900812A3 SU 802874898 A SU802874898 A SU 802874898A SU 2874898 A SU2874898 A SU 2874898A SU 900812 A3 SU900812 A3 SU 900812A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dimethoxy
- furoyl
- piperazinyl
- amino
- producing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 13
- VBUBADWLHFZFDK-UHFFFAOYSA-N quinazoline;hydrochloride Chemical compound Cl.N1=CN=CC2=CC=CC=C21 VBUBADWLHFZFDK-UHFFFAOYSA-N 0.000 title 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract 4
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract 2
- -1 2-furoyl Chemical group 0.000 claims description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/84—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Cephalosporin Compounds (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ ГИДРОХЛОРИДА 6,7-Д№1ЕТОКСИ-4-АМИНО-2- Г4- ( 2-ФУРОШ1) -1 -ШШЕРАЗИНИЛ -ХИНАЗОЛННА
1
Изобретение относитс к новому способу получени гидрохлорида 6,7-диметокси-4-амино-2-С4- (2-фуроил)-1-пнперазиннл -хинозолина формулы
Vr - -lLlit)
который обладает противогипертоничес КИМ действием, и может найти примене ние в медицине.
Известен способ получени 6,7-диметокси-4-амино-2-14- (2-фуроил)-1-пиперазинил -хиназолин гидрохлори да, формулы I, заключающийс в том, что соединение формулы
СИзО
(1а)
где Q - циангруппа или -C(-NH)-NH4группу или его соль, подвергают
взаимодействию с пиперазином формулы
,0
/
А-Ы V1-W- J I5)
где АC(NH)-0-CjHj-группу,
при 50-180 с, в присутствии основного катализатора Ul
10
Недостатком известного способа вл етс сложность технологии процесса , а также трудоемкость очистки 15 целевого продукта.
Цель изобретени - упрощение прс1цесса .
Поставленна цель достигаетс
20 предлагаемым способом получени соединени формулы I, заключающимс в том, что провод т внутримолекул рное замыкание мeтил-N-(3,4-димeтoкcи-6
Claims (2)
- Формула изобретения I. Способ получения гидрохлорида 6,7-диметокси-4-амино 2-Г4-(2-фуроил)-1-пиперазинил] -хиназолина формулы I о т л и ч а ю щ и й с я тем, что, с целью упрощения процесса, проводят внутримолекулярное замыкание метил-N-(3,4-диметокси-6-цианофеннл)- [4-(2-фуронл)-1-пиперазннил]-тиоформамкдата формулы ItМ с 30-40 моль хлористого аммония в формамиде при 100-140еС.
- ‘2. Способ по η.I, о т л и ч а ю щ ий с я тем, что процесс проводят при 120®С в течение 15-20 ч.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI790320A FI67699C (fi) | 1979-01-31 | 1979-01-31 | Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolinhydroklorid med blodtryckssaenkande verkan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU900812A3 true SU900812A3 (ru) | 1982-01-23 |
Family
ID=8512343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802874898A SU900812A3 (ru) | 1979-01-31 | 1980-01-30 | Способ получени гидрохлорида 6,7-диметокси-4-амино-2-[4-(2-фуроил)-1-пиперазинил-ХИНАЗОЛИНА |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4271300A (ru) |
| JP (1) | JPS55104280A (ru) |
| AT (1) | AT374475B (ru) |
| BE (1) | BE881297A (ru) |
| CA (1) | CA1128945A (ru) |
| CH (1) | CH644605A5 (ru) |
| CS (1) | CS214692B2 (ru) |
| DD (1) | DD148952A1 (ru) |
| DE (1) | DE3002553A1 (ru) |
| DK (1) | DK158352C (ru) |
| FI (1) | FI67699C (ru) |
| FR (1) | FR2447920A1 (ru) |
| GB (1) | GB2041932B (ru) |
| HU (1) | HU181016B (ru) |
| NL (1) | NL190701C (ru) |
| NO (1) | NO152298C (ru) |
| PL (1) | PL126994B1 (ru) |
| SE (1) | SE430692B (ru) |
| SU (1) | SU900812A3 (ru) |
| YU (1) | YU41498B (ru) |
| ZA (1) | ZA80501B (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI70411C (fi) * | 1980-12-29 | 1986-09-19 | Pfizer | Foerfarande foer framstaellning av nya antihypertensiva 4-amino-6,7-dimetoxi-2-piperazinokinazolin derivat |
| FI79107C (fi) * | 1984-06-25 | 1989-11-10 | Orion Yhtymae Oy | Foerfarande foer framstaellning av stabil -form av prazosinhydroklorid. |
| US4601897A (en) * | 1985-11-06 | 1986-07-22 | Pfizer Inc. | Prazosin-pirbuterol combination for bronchodilation |
| AT384218B (de) * | 1985-12-04 | 1987-10-12 | Gerot Pharmazeutika | Verfahren zur herstellung von neuen chinazolin-derivaten |
| YU70890A (en) * | 1989-04-21 | 1992-05-28 | Egyt Gyogyszervegyeszeti Gyar | Process for obtaining quinazoline derivatives |
| CA2077252C (en) * | 1992-08-31 | 2001-04-10 | Khashayar Karimian | Methods of making ureas and guanidines, and intermediates therefor |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3511836A (en) * | 1967-12-13 | 1970-05-12 | Pfizer & Co C | 2,4,6,7-tetra substituted quinazolines |
| GB1390015A (en) * | 1971-05-07 | 1975-04-09 | Koninklijke Pharma Fab Nv | 4-amino-quinazoline compounds |
| US3935213A (en) * | 1973-12-05 | 1976-01-27 | Pfizer Inc. | Process for hypotensive 4-amino-2-(piperazin-1-yl) quinazoline derivatives |
| US4092315A (en) * | 1976-03-01 | 1978-05-30 | Pfizer Inc. | Novel crystalline forms of prazosin hydrochloride |
| FI58125C (fi) * | 1976-12-15 | 1985-01-02 | Orion Yhtymae Oy | Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande vekan |
| FI58124C (fi) * | 1976-12-15 | 1980-12-10 | Orion Yhtymae Oy | Ny mellanprodukt 3,4-dimetoxi-6-(4-(2-furoyl)-1-piperazinyltiokarbamido)-bensonitril foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande verkan |
-
1979
- 1979-01-31 FI FI790320A patent/FI67699C/fi not_active IP Right Cessation
- 1979-12-27 NO NO794279A patent/NO152298C/no unknown
-
1980
- 1980-01-09 CA CA343,361A patent/CA1128945A/en not_active Expired
- 1980-01-09 CH CH12180A patent/CH644605A5/de not_active IP Right Cessation
- 1980-01-09 US US06/110,589 patent/US4271300A/en not_active Expired - Lifetime
- 1980-01-10 YU YU58/80A patent/YU41498B/xx unknown
- 1980-01-15 AT AT0019580A patent/AT374475B/de not_active IP Right Cessation
- 1980-01-16 NL NL8000289A patent/NL190701C/xx not_active IP Right Cessation
- 1980-01-23 BE BE0/199070A patent/BE881297A/fr not_active IP Right Cessation
- 1980-01-25 DE DE19803002553 patent/DE3002553A1/de active Granted
- 1980-01-28 ZA ZA00800501A patent/ZA80501B/xx unknown
- 1980-01-28 CS CS80588A patent/CS214692B2/cs unknown
- 1980-01-29 HU HU8080182A patent/HU181016B/hu not_active IP Right Cessation
- 1980-01-29 GB GB8002903A patent/GB2041932B/en not_active Expired
- 1980-01-30 SU SU802874898A patent/SU900812A3/ru active
- 1980-01-30 FR FR8001991A patent/FR2447920A1/fr active Granted
- 1980-01-30 PL PL1980221684A patent/PL126994B1/pl unknown
- 1980-01-30 JP JP1081580A patent/JPS55104280A/ja active Granted
- 1980-01-31 DK DK042680A patent/DK158352C/da not_active IP Right Cessation
- 1980-01-31 SE SE8000777A patent/SE430692B/sv unknown
- 1980-01-31 DD DD80218776A patent/DD148952A1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DD148952A1 (de) | 1981-06-17 |
| GB2041932A (en) | 1980-09-17 |
| AT374475B (de) | 1984-04-25 |
| FI67699C (fi) | 1985-05-10 |
| ZA80501B (en) | 1981-02-25 |
| PL126994B1 (en) | 1983-09-30 |
| JPS55104280A (en) | 1980-08-09 |
| CA1128945A (en) | 1982-08-03 |
| SE8000777L (sv) | 1980-08-01 |
| YU5880A (en) | 1983-02-28 |
| JPS6310955B2 (ru) | 1988-03-10 |
| HU181016B (en) | 1983-05-30 |
| US4271300A (en) | 1981-06-02 |
| DK42680A (da) | 1980-08-01 |
| SE430692B (sv) | 1983-12-05 |
| ATA19580A (de) | 1983-09-15 |
| DE3002553C2 (ru) | 1988-10-27 |
| NL190701C (nl) | 1994-07-01 |
| GB2041932B (en) | 1982-10-27 |
| NL190701B (nl) | 1994-02-01 |
| NO794279L (no) | 1980-08-01 |
| DE3002553A1 (de) | 1980-08-07 |
| CH644605A5 (de) | 1984-08-15 |
| NO152298C (no) | 1985-09-04 |
| FR2447920A1 (fr) | 1980-08-29 |
| DK158352B (da) | 1990-05-07 |
| NL8000289A (nl) | 1980-08-04 |
| DK158352C (da) | 1990-10-08 |
| FR2447920B1 (ru) | 1982-12-03 |
| NO152298B (no) | 1985-05-28 |
| BE881297A (fr) | 1980-05-16 |
| YU41498B (en) | 1987-08-31 |
| FI67699B (fi) | 1985-01-31 |
| FI790320A (fi) | 1980-08-01 |
| CS214692B2 (en) | 1982-05-28 |
| PL221684A1 (ru) | 1980-10-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TR200003632T2 (tr) | Benzotiyepin-1,1-dioksid türevleri, üretim yöntemi, bunları içeren ilaçlar. | |
| SU900812A3 (ru) | Способ получени гидрохлорида 6,7-диметокси-4-амино-2-[4-(2-фуроил)-1-пиперазинил-ХИНАЗОЛИНА | |
| TR200103352T2 (tr) | Kinas pirolotriazin inhibitörleri | |
| ATE26112T1 (de) | Isochinolin-sulfonamidderivate und verfahren fuer ihre herstellung. | |
| ATE144774T1 (de) | Verfahren zur herstellung von pyrrolo (2,3- d)pyrimidinen | |
| TR199800608A2 (en) | Propanolamin t�revleri, bunlar�n �retim usul�. | |
| ATE19776T1 (de) | Neue substituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel. | |
| ES544748A0 (es) | Procedimiento para preparar cetonas heterociclicas nitroge- nadas con anillo de siete miembros y condensadas | |
| FI66610C (fi) | Foerfarande foer framstaellning av 2-(4-furoylpiperazin-1-yl)-4-amino-6,7-dimetoxikinazolin | |
| RU2004116345A (ru) | Способы получения замещенных бициклических производных, полезных для лечения патологического роста клеток | |
| EP0146642B1 (de) | Verfahren zur Herstellung von 4-Amino-6,7-dimethoxy-2-(4-(furo-2-yl)-piperazin-1-yl)-chinazolin und dessen physiologisch annehmbarer Salze | |
| CA2211646A1 (en) | Substituted phenyl compounds as endothelin antagonists | |
| SE7413856L (ru) | ||
| Kitagawa et al. | Equilibrium Studies of 5-Substituted 4-Hydroxy-2-methylpyrimidines. I. The Ionization Constants in Aqueous Solution | |
| ES8604488A1 (es) | Un procedimiento para la preparacion de un derivado de ace- tileno | |
| RU94046247A (ru) | Способ получения практически беспыльного гранулята из тетрагидро-3,5-диметил-1,3,5-тиадиазин-2-тиона | |
| EA200200733A1 (ru) | Новые гетероарильные производные, их получение и применение | |
| EP0172509A3 (de) | Verfahren zur Herstellung optisch aktiver, substituierter 1,4-Dihydropyridine und ihre Verwendung als Arzneimittel | |
| EP0229944A3 (en) | Novel tetrahydroisoquinoline derivatives | |
| SU724503A1 (ru) | Ариламиды о-нитробензолсульфокислоты, про вл ющие диуретическую активность | |
| SU650593A1 (ru) | Стимул тор роста растений | |
| TR200101780T2 (tr) | Yeni ß-amido ve ß-sülfonamido karboksilik asit türevleri. | |
| SU1214667A1 (ru) | @ -Замещенные 3/5/- метилпиразолы как ингибиторы нитрификации азотных удобрений | |
| TR200001365T2 (tr) | Yeni heterosiklik ikame edilmiş a-hidroksikarbonik asit türevleri | |
| 北川隆康 et al. | Equilibrium Studies of 5-Substituted 4-Hydroxy-2-methylpyrimidines. I. The Ionization Constants in Aqueous Solution |