CS234018B2 - Method of 3,5-diammino-6-1,2,4-triazine derivatives making - Google Patents

Method of 3,5-diammino-6-1,2,4-triazine derivatives making Download PDF

Info

Publication number: CS234018B2
Authority: CS; Czechoslovakia
Prior art keywords: hydrogen; chlorine; bromine; compounds; trifluoromethyl
Prior art date: 1979-06-01

Application number

CS803829A

Other languages

Czech (cs)

English (en)

Inventor

Martin G Baxter

Albert R Elphick

Alistair A Miller

David A Sawyer

Original Assignee

Wellcome Found

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.)

1979-06-01

Filing date

1980-05-30

Publication date

1985-03-14

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10505597&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CS234018(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1980-05-30 Application filed by Wellcome Found filed Critical Wellcome Found

1985-03-14 Publication of CS234018B2 publication Critical patent/CS234018B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 39
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
239000001257 hydrogen Substances 0.000 claims abstract description 31
229910052794 bromium Inorganic materials 0.000 claims abstract description 20
239000000460 chlorine Substances 0.000 claims abstract description 20
229910052801 chlorine Inorganic materials 0.000 claims abstract description 20
-1 di-substituted aminomethyleneamino Chemical group 0.000 claims abstract description 19
150000002431 hydrogen Chemical group 0.000 claims abstract description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 14
239000002253 acid Substances 0.000 claims abstract description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
125000001153 fluoro group Chemical group F* 0.000 claims description 7
IGICDOGCTIXJCD-UHFFFAOYSA-N 6-phenyl-1,2,4-triazine-3,5-diamine Chemical class NC1=NC(N)=NN=C1C1=CC=CC=C1 IGICDOGCTIXJCD-UHFFFAOYSA-N 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 3
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125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 abstract description 18
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238000004519 manufacturing process Methods 0.000 abstract description 2
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239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000008234 soft water Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000010257 thawing Methods 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having 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
- C07D253/075—Two hetero atoms, in positions 3 and 5
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Neurology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Neurosurgery (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CS803829A 1979-06-01 1980-05-30 Method of 3,5-diammino-6-1,2,4-triazine derivatives making CS234018B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7919257		1979-06-01

Publications (1)

Publication Number	Publication Date
CS234018B2 true CS234018B2 (en)	1985-03-14

Family

ID=10505597

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS803829A CS234018B2 (en)	1979-06-01	1980-05-30	Method of 3,5-diammino-6-1,2,4-triazine derivatives making

Country Status (30)

Country	Link
US (2)	US4486354A (ar)
EP (2)	EP0059987B1 (ar)
JP (2)	JPS5625169A (ar)
AR (1)	AR227521A1 (ar)
AT (1)	AT370097B (ar)
AU (2)	AU530999B2 (ar)
BG (1)	BG60427B2 (ar)
CA (1)	CA1112643A (ar)
CS (1)	CS234018B2 (ar)
CZ (1)	CZ384891A3 (ar)
DD (1)	DD151309A5 (ar)
DK (1)	DK153787C (ar)
ES (1)	ES491998A0 (ar)
FI (1)	FI67844C (ar)
GE (1)	GEP19960470B (ar)
GR (1)	GR68380B (ar)
HU (1)	HU182086B (ar)
IE (1)	IE49823B1 (ar)
IL (1)	IL60201A (ar)
IT (1)	IT1147087B (ar)
MX (1)	MX9202962A (ar)
MY (1)	MY8500062A (ar)
NL (1)	NL950007I2 (ar)
NZ (1)	NZ193890A (ar)
PL (1)	PL124029B1 (ar)
SU (1)	SU1055331A3 (ar)
UA (1)	UA5576A1 (ar)
YU (1)	YU145680A (ar)
ZA (1)	ZA803250B (ar)
ZW (1)	ZW12980A1 (ar)

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GB759014A (en) *	1952-02-26	1956-10-10	Wellcome Found	Improvements in triazines and their manufacture
AT190941B (de) *	1954-09-22	1957-07-25	Chemie Linz Ag	Verfahren zur Herstellung neuer Guanylhydrazone
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US4311701A (en) *	1979-08-16	1982-01-19	Barbara Roth	Treatment of convulsions with triazines

1980
- 1980-05-30 PL PL1980224633A patent/PL124029B1/pl unknown
- 1980-05-30 IE IE1126/80A patent/IE49823B1/en not_active IP Right Cessation
- 1980-05-30 HU HU801364A patent/HU182086B/hu unknown
- 1980-05-30 AU AU58906/80A patent/AU530999B2/en not_active Expired
- 1980-05-30 ES ES491998A patent/ES491998A0/es active Granted
- 1980-05-30 IL IL60201A patent/IL60201A/xx unknown
- 1980-05-30 AT AT0289680A patent/AT370097B/de not_active IP Right Cessation
- 1980-05-30 GR GR62081A patent/GR68380B/el unknown
- 1980-05-30 ZW ZW129/80A patent/ZW12980A1/xx unknown
- 1980-05-30 CA CA353,081A patent/CA1112643A/en not_active Expired
- 1980-05-30 EP EP82102293A patent/EP0059987B1/en not_active Expired
- 1980-05-30 DK DK233880A patent/DK153787C/da active
- 1980-05-30 FI FI801758A patent/FI67844C/fi not_active IP Right Cessation
- 1980-05-30 DD DD80221474A patent/DD151309A5/de unknown
- 1980-05-30 CS CS803829A patent/CS234018B2/cs unknown
- 1980-05-30 JP JP7158080A patent/JPS5625169A/ja active Granted
- 1980-05-30 EP EP80103032A patent/EP0021121B1/en not_active Expired
- 1980-05-30 NZ NZ193890A patent/NZ193890A/en unknown
- 1980-05-30 IT IT48848/80A patent/IT1147087B/it active Protection Beyond IP Right Term
- 1980-05-30 ZA ZA00803250A patent/ZA803250B/xx unknown
- 1980-05-30 AR AR281263A patent/AR227521A1/es active
- 1980-05-31 YU YU01456/80A patent/YU145680A/xx unknown
- 1980-06-02 SU SU802932704A patent/SU1055331A3/ru active
- 1980-06-02 UA UA2932704A patent/UA5576A1/uk unknown
1981
- 1981-10-05 US US06/308,805 patent/US4486354A/en not_active Expired - Lifetime
1983
- 1983-04-28 AU AU14051/83A patent/AU566870B2/en not_active Expired
1984
- 1984-02-27 US US06/583,286 patent/US4602017A/en not_active Expired - Lifetime
1985
- 1985-06-04 JP JP12137085A patent/JPS6133163A/ja active Granted
- 1985-12-30 MY MY62/85A patent/MY8500062A/xx unknown
1991
- 1991-12-17 CZ CS913848A patent/CZ384891A3/cs unknown
1992
- 1992-06-17 MX MX9202962A patent/MX9202962A/es unknown
1993
- 1993-07-29 BG BG097992A patent/BG60427B2/bg unknown
1994
- 1994-05-16 GE GEAP19941909A patent/GEP19960470B/en unknown
1995
- 1995-04-28 NL NL950007C patent/NL950007I2/nl unknown

Also Published As

Publication number	Publication date
AU5890680A (en)	1980-12-04
US4602017A (en)	1986-07-22
UA5576A1 (uk)	1994-12-28
DK233880A (da)	1980-12-02
GR68380B (ar)	1981-12-28
CZ384891A3 (en)	1993-10-13
DK153787C (da)	1989-01-16
JPS6133163A (ja)	1986-02-17
MY8500062A (en)	1985-12-31
AU566870B2 (en)	1987-11-05
EP0021121B1 (en)	1983-05-11
IT1147087B (it)	1986-11-19
FI67844B (fi)	1985-02-28
PL224633A1 (ar)	1981-02-13
IE801126L (en)	1980-12-01
CA1112643A (en)	1981-11-17
ATA289680A (de)	1982-07-15
IL60201A0 (en)	1980-07-31
EP0059987B1 (en)	1985-08-14
AR227521A1 (es)	1982-11-15
FI67844C (fi)	1985-06-10
IT8048848A0 (it)	1980-05-30
US4486354A (en)	1984-12-04
YU145680A (en)	1983-02-28
ES8104993A1 (es)	1981-05-16
ZA803250B (en)	1982-01-27
HU182086B (en)	1983-12-28
DD151309A5 (de)	1981-10-14
JPH0144179B2 (ar)	1989-09-26
IE49823B1 (en)	1985-12-25
MX9202962A (es)	1992-07-01
NL950007I1 (nl)	1995-06-16
IL60201A (en)	1984-05-31
NL950007I2 (nl)	1997-02-03
FI801758A7 (fi)	1980-12-02
PL124029B1 (en)	1982-12-31
NZ193890A (en)	1984-07-06
ES491998A0 (es)	1981-05-16
EP0021121A1 (en)	1981-01-07
AU530999B2 (en)	1983-08-04
SU1055331A3 (ru)	1983-11-15
JPH0144706B2 (ar)	1989-09-29
EP0059987A1 (en)	1982-09-15
JPS5625169A (en)	1981-03-10
GEP19960470B (en)	1996-08-29
DK153787B (da)	1988-09-05
BG60427B2 (bg)	1995-03-31
ZW12980A1 (en)	1982-01-06
AT370097B (de)	1983-02-25

Publication	Publication Date	Title
EP0021121B1 (en)	1983-05-11	1,2,4-triazine derivatives, process for preparing such compounds and pharmaceutical compositions containing them
KR920006781B1 (ko)	1992-08-17	디하이드로 피리다진온 유도체를 제조하는 방법
CA1261328A (en)	1989-09-26	Triazine compounds having cardiovascular activity
JPH0316344B2 (ar)	1991-03-05
OA10946A (en)	2003-02-27	Substituted 3,5-diphenyl-1,2,4-triazoles and theiruse as pharmaceutical metal chelators
US3560566A (en)	1971-02-02	Diphenyl-ureas,-thioureas,-guanidines and -parabanic acids
US4560687A (en)	1985-12-24	Substituted aromatic compounds
CA1108619A (en)	1981-09-08	4-hydroxy-2-benzimidazolinone derivatives and the preparation thereof
HU181608B (en)	1983-10-28	Process for producing imidazo-thieno-pyrimidine derivatives
CA1133938A (en)	1982-10-19	Substituted aromatic compounds
US4517182A (en)	1985-05-14	3-(Haloethyl)-4-oxopyrazolo-[5,1-d]-1,2,3,5-tetrazine-8-carboxamide composition
US3139431A (en)	1964-06-30	6-(5-nitro-2-furyl) azauracil
US4504475A (en)	1985-03-12	3-(Haloethyl)-4-oxopyrazolo[5,1-D]-1,2,3,5-tetrazine-8-carboxamide compounds
JPH0320276A (ja)	1991-01-29	抗痙攣性ピラジン
US3631174A (en)	1971-12-28	4 5-heterocyclic substituted-6 7-dihydrobenzothiophenes
KR970003126B1 (ko)	1997-03-14	디티올란 유도체
US2978457A (en)	1961-04-04	5-acylamido-4-substituted-thiazole-2-sulfonamides having diuretic properties
NZ205891A (en)	1986-02-21	4-hydroxy-2h-1,2-benzothiazine-3-carboxamide 1,1-dioxides and pharmaceutical compositions
US3367931A (en)	1968-02-06	1-(2-hydroxy-3-methoxypropyl)-3-(5-nitrofurfurylideneamino)-2-imidazolidinone
US3496175A (en)	1970-02-17	Substituted imidazotriazines
US3445465A (en)	1969-05-20	3-(2-fluorophenyl)-1,2,3-benzotriazin-4-one
JPH02501064A (ja)	1990-04-12	強心作用を有するイミダゾリルフエニルピロール‐２‐オン
JPH07116180B2 (ja)	1995-12-13	ジチオ−ル誘導体及びその製法並びにその用途
DE2306770A1 (de)	1974-09-26	Neue 2-acylamino-5-phenyl-4h-3,5dihydro-1,5-benzodiazepin-4-one