NL8303032A - Nieuwe geacyleerde 1,2,4-triazoolderivaten, hun intermediairen, werkwijze voor de bereiding ervan en het 1,2,4-triazoolderivaat bevattend geneesmiddel. - Google Patents

Nieuwe geacyleerde 1,2,4-triazoolderivaten, hun intermediairen, werkwijze voor de bereiding ervan en het 1,2,4-triazoolderivaat bevattend geneesmiddel. Download PDF

Info

Publication number: NL8303032A
Authority: NL; Netherlands
Prior art keywords: general formula; compound; methyl; meaning; amino
Prior art date: 1982-09-01

Application number

NL8303032A

Other languages

English (en)

Dutch (nl)

Original Assignee

Biogal Gyogyszergyar

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.)

1982-09-01

Filing date

1983-08-31

Publication date

1984-04-02

1983-08-31 Application filed by Biogal Gyogyszergyar filed Critical Biogal Gyogyszergyar

1984-04-02 Publication of NL8303032A publication Critical patent/NL8303032A/nl

Links

238000000034 method Methods 0.000 title claims description 26
229940126601 medicinal product Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
-1 hydroxy, amino Chemical group 0.000 claims description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
230000001790 virustatic effect Effects 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
239000011230 binding agent Substances 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
238000002844 melting Methods 0.000 claims description 6
230000008018 melting Effects 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
230000010933 acylation Effects 0.000 claims description 3
238000005917 acylation reaction Methods 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
239000003701 inert diluent Substances 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 2
239000004480 active ingredient Substances 0.000 claims 1
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
239000003755 preservative agent Substances 0.000 claims 1
241000700605 Viruses Species 0.000 description 12
239000000203 mixture Substances 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
229910052740 iodine Inorganic materials 0.000 description 8
239000011630 iodine Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
238000004113 cell culture Methods 0.000 description 6
XGWWZKBCQLBJNH-UHFFFAOYSA-N 3-methylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound CSC1=NN=C(N)N1 XGWWZKBCQLBJNH-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
241000712079 Measles morbillivirus Species 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
DCFOYOSOUSTEAG-UHFFFAOYSA-N 2-chloro-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzamide Chemical compound CSC1=NNC(NC(=O)C=2C(=CC=CC=2)Cl)=N1 DCFOYOSOUSTEAG-UHFFFAOYSA-N 0.000 description 3
GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000003013 cytotoxicity Effects 0.000 description 3
231100000135 cytotoxicity Toxicity 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
230000035755 proliferation Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
241000712461 unidentified influenza virus Species 0.000 description 3
ANCYIKYMJVRRJH-UHFFFAOYSA-N (5-amino-3-methylsulfanyl-1,2,4-triazol-1-yl)-(2-methylphenyl)methanone Chemical compound N1=C(SC)N=C(N)N1C(=O)C1=CC=CC=C1C ANCYIKYMJVRRJH-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000007541 cellular toxicity Effects 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
RDAJAIIWUXPLPB-UHFFFAOYSA-N (5-amino-3-methylsulfanyl-1,2,4-triazol-1-yl)-(4-chlorophenyl)methanone Chemical compound N1=C(SC)N=C(N)N1C(=O)C1=CC=C(Cl)C=C1 RDAJAIIWUXPLPB-UHFFFAOYSA-N 0.000 description 1
WAWCVJQGMFGSOH-UHFFFAOYSA-N (5-amino-3-methylsulfanyl-1,2,4-triazol-1-yl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C(N)=NC(SC)=N1 WAWCVJQGMFGSOH-UHFFFAOYSA-N 0.000 description 1
VQRBXYBBGHOGFT-UHFFFAOYSA-N 1-(chloromethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CCl VQRBXYBBGHOGFT-UHFFFAOYSA-N 0.000 description 1
UCDUHAURQVKFJE-UHFFFAOYSA-N 2-bromo-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzamide Chemical compound CSC1=NNC(NC(=O)C=2C(=CC=CC=2)Br)=N1 UCDUHAURQVKFJE-UHFFFAOYSA-N 0.000 description 1
125000005999 2-bromoethyl group Chemical group 0.000 description 1
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
DZCLOAYHWVZIHH-UHFFFAOYSA-N 2-hydroxy-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzamide Chemical compound CSC1=NNC(NC(=O)C=2C(=CC=CC=2)O)=N1 DZCLOAYHWVZIHH-UHFFFAOYSA-N 0.000 description 1
AZAUSLJPGDVATA-UHFFFAOYSA-N 2-methyl-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzamide Chemical compound CSC1=NNC(NC(=O)C=2C(=CC=CC=2)C)=N1 AZAUSLJPGDVATA-UHFFFAOYSA-N 0.000 description 1
APJVLEWAJUWHQH-UHFFFAOYSA-N 2-methyl-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzenecarbothioamide Chemical compound CSC1=NNC(NC(=S)C=2C(=CC=CC=2)C)=N1 APJVLEWAJUWHQH-UHFFFAOYSA-N 0.000 description 1
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
208000009889 Herpes Simplex Diseases 0.000 description 1
241001135569 Human adenovirus 5 Species 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VUTHPBSGBCYZFX-UHFFFAOYSA-N [2-(5-amino-3-methylsulfanyl-1,2,4-triazole-1-carbonyl)phenyl] acetate Chemical compound N1=C(SC)N=C(N)N1C(=O)C1=CC=CC=C1OC(C)=O VUTHPBSGBCYZFX-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000013043 chemical agent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
HUDLSVXTUBASBN-UHFFFAOYSA-N n-(3-ethylsulfanyl-1h-1,2,4-triazol-5-yl)-2-methylbenzamide Chemical compound CCSC1=NNC(NC(=O)C=2C(=CC=CC=2)C)=N1 HUDLSVXTUBASBN-UHFFFAOYSA-N 0.000 description 1
ZTJAGNZJYVNBSD-UHFFFAOYSA-N n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)-2-nitrobenzamide Chemical compound CSC1=NNC(NC(=O)C=2C(=CC=CC=2)[N+]([O-])=O)=N1 ZTJAGNZJYVNBSD-UHFFFAOYSA-N 0.000 description 1
231100000065 noncytotoxic Toxicity 0.000 description 1
230000002020 noncytotoxic effect Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
239000012071 phase Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
241000701161 unidentified adenovirus Species 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
Virology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NL8303032A 1982-09-01 1983-08-31 Nieuwe geacyleerde 1,2,4-triazoolderivaten, hun intermediairen, werkwijze voor de bereiding ervan en het 1,2,4-triazoolderivaat bevattend geneesmiddel. NL8303032A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU279782		1982-09-01
HU822797A HU191475B (en)	1982-09-01	1982-09-01	Process for producing new acylized 1,2,4-triazole derivatives

Publications (1)

Publication Number	Publication Date
NL8303032A true NL8303032A (nl)	1984-04-02

Family

ID=10961139

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8303032A NL8303032A (nl)	1982-09-01	1983-08-31	Nieuwe geacyleerde 1,2,4-triazoolderivaten, hun intermediairen, werkwijze voor de bereiding ervan en het 1,2,4-triazoolderivaat bevattend geneesmiddel.

Country Status (11)

Country	Link
US (1)	US4537899A (de)
JP (1)	JPS5993063A (de)
AT (1)	AT384425B (de)
BE (1)	BE897607A (de)
CH (1)	CH655105A5 (de)
DE (1)	DE3331591A1 (de)
FR (1)	FR2532311B1 (de)
GB (1)	GB2130200B (de)
HU (1)	HU191475B (de)
NL (1)	NL8303032A (de)
SE (1)	SE454987B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60239362A (ja) *	1982-12-16	1985-11-28	アルミニウム　カンパニ−　オブ　アメリカ	ベ−タシリコンアルミニウムオキシナイトライド耐火材料を製造する方法
EP1223932A4 (de) *	1999-10-01	2003-01-15	Smithkline Beecham Corp	Verbindungen und verfahren
KR100849021B1 (ko)	2007-06-19	2008-07-29	(주)더페이스샵코리아	카페익산 유도체 및 이를 함유하는 조성물
ES2882807T3 (es)	2011-09-16	2021-12-02	Novartis Ag	Heterociclil carboxamidas N-sustituidas

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD113362A1 (de) *	1974-02-07	1975-06-05
JPS5559463A (en) *	1978-10-30	1980-05-02	Konishiroku Photo Ind Co Ltd	Color photographic material
MA19269A1 (fr) *	1980-09-16	1982-04-01	Lilly Co Eli	Perfectionnement relatif a des derives de n-arylbenzamides .

1982
- 1982-09-01 HU HU822797A patent/HU191475B/hu not_active IP Right Cessation
1983
- 1983-08-25 US US06/526,694 patent/US4537899A/en not_active Expired - Fee Related
- 1983-08-29 BE BE1010858A patent/BE897607A/fr unknown
- 1983-08-31 FR FR838313963A patent/FR2532311B1/fr not_active Expired - Lifetime
- 1983-08-31 NL NL8303032A patent/NL8303032A/nl not_active Application Discontinuation
- 1983-08-31 JP JP58158128A patent/JPS5993063A/ja active Pending
- 1983-08-31 CH CH4765/83A patent/CH655105A5/de not_active IP Right Cessation
- 1983-08-31 AT AT0311083A patent/AT384425B/de not_active IP Right Cessation
- 1983-08-31 SE SE8304715A patent/SE454987B/sv not_active IP Right Cessation
- 1983-09-01 DE DE3331591A patent/DE3331591A1/de not_active Withdrawn
- 1983-09-01 GB GB08323422A patent/GB2130200B/en not_active Expired

Also Published As

Publication number	Publication date
BE897607A (fr)	1984-02-29
SE8304715D0 (sv)	1983-08-31
FR2532311B1 (fr)	1990-05-11
GB2130200A (en)	1984-05-31
AT384425B (de)	1987-11-10
GB2130200B (en)	1986-05-08
US4537899A (en)	1985-08-27
CH655105A5 (de)	1986-03-27
HU191475B (en)	1987-02-27
JPS5993063A (ja)	1984-05-29
ATA311083A (de)	1987-04-15
SE8304715L (sv)	1984-03-02
DE3331591A1 (de)	1984-03-01
FR2532311A1 (fr)	1984-03-02
GB8323422D0 (en)	1983-10-05
SE454987B (sv)	1988-06-13

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1990-04-02	BV	The patent application has lapsed

Publication	Publication Date	Title
Karabasanagouda et al.	2007	Synthesis and antimicrobial activities of some novel 1, 2, 4-triazolo [3, 4-b]-1, 3, 4-thiadiazoles and 1, 2, 4-triazolo [3, 4-b]-1, 3, 4-thiadiazines carrying thioalkyl and sulphonyl phenoxy moieties
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NL8303032A (nl)	1984-04-02	Nieuwe geacyleerde 1,2,4-triazoolderivaten, hun intermediairen, werkwijze voor de bereiding ervan en het 1,2,4-triazoolderivaat bevattend geneesmiddel.
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