BE826816R - Nouveaux thiadiazoles, leur preparation et medicaments les contenant - Google Patents

Nouveaux thiadiazoles, leur preparation et medicaments les contenant

Info

Publication number: BE826816R
Authority: BE; Belgium
Prior art keywords: emi; thiadiazole; formula; compounds; amino
Prior art date: 1974-03-20

Application number

BE154447A

Other languages

English (en)

French (fr)

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.)

1974-03-20

Filing date

1975-03-18

Publication date

1975-09-18

1975-03-18 Application filed filed Critical

1975-09-18 Application granted granted Critical

1975-09-18 Publication of BE826816R publication Critical patent/BE826816R/fr

Links

150000004867 thiadiazoles Chemical class 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title description 3
229940126601 medicinal product Drugs 0.000 title 1
150000001875 compounds Chemical group 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
150000007524 organic acids Chemical class 0.000 claims description 8
235000005985 organic acids Nutrition 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
239000002249 anxiolytic agent Substances 0.000 claims description 7
229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
239000011707 mineral Substances 0.000 claims description 7
150000007522 mineralic acids Chemical class 0.000 claims description 7
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 7
229940079593 drug Drugs 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000002841 Lewis acid Substances 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
229910052801 chlorine Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
150000007517 lewis acids Chemical class 0.000 claims description 4
RRXDVGPGAOJOFL-UHFFFAOYSA-N 5-[[3-(trifluoromethyl)phenyl]methyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CC1=CC=CC(C(F)(F)F)=C1 RRXDVGPGAOJOFL-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
239000005554 hypnotics and sedatives Substances 0.000 claims 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
229910052731 fluorine Inorganic materials 0.000 claims 3
239000011737 fluorine Chemical group 0.000 claims 3
229910052739 hydrogen Inorganic materials 0.000 claims 3
239000001257 hydrogen Substances 0.000 claims 3
VOVGTRUVYKHYJA-UHFFFAOYSA-N 5-[2-[3-(trifluoromethyl)phenyl]ethyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CCC1=CC=CC(C(F)(F)F)=C1 VOVGTRUVYKHYJA-UHFFFAOYSA-N 0.000 claims 2
239000004480 active ingredient Substances 0.000 claims 2
239000012458 free base Substances 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 1
QHQVBZWCNJVWJZ-UHFFFAOYSA-N 5-[[2,5-dichloro-3-(trifluoromethyl)phenyl]methyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CC1=CC(Cl)=CC(C(F)(F)F)=C1Cl QHQVBZWCNJVWJZ-UHFFFAOYSA-N 0.000 claims 1
DNKNUHGUGHSKKO-UHFFFAOYSA-N 5-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1CC1=CC=C(C(F)(F)F)C=C1 DNKNUHGUGHSKKO-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
QVSABOFUEHNNTC-UHFFFAOYSA-N NC=1SC(=NN=1)CC1=CC(=C(C=C1)C(F)(F)F)C(F)(F)F Chemical compound NC=1SC(=NN=1)CC1=CC(=C(C=C1)C(F)(F)F)C(F)(F)F QVSABOFUEHNNTC-UHFFFAOYSA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
239000013543 active substance Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
-1 for example Chemical class 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
230000000694 effects Effects 0.000 description 4
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 4
238000007912 intraperitoneal administration Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
230000004799 sedative–hypnotic effect Effects 0.000 description 4
239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
208000010513 Stupor Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000008101 lactose Substances 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
230000007958 sleep Effects 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
206010011985 Decubitus ulcer Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
206010062519 Poor quality sleep Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
230000006399 behavior Effects 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
235000010487 tragacanth Nutrition 0.000 description 2
239000000196 tragacanth Substances 0.000 description 2
229940116362 tragacanth Drugs 0.000 description 2
239000003204 tranquilizing agent Substances 0.000 description 2
230000002936 tranquilizing effect Effects 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
UEGBWDUVDAKUGA-UHFFFAOYSA-N 2,6,10-trimethylundec-9-enal Chemical compound CC(C)=CCCC(C)CCCC(C)C=O UEGBWDUVDAKUGA-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
BLXXCCIBGGBDHI-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C(F)(F)F)=C1 BLXXCCIBGGBDHI-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000282668 Cebus Species 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
231100000111 LD50 Toxicity 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
STIMORLKYIPIAQ-UHFFFAOYSA-N [[2-[3-(trifluoromethyl)phenyl]acetyl]amino]thiourea Chemical compound NC(=S)NNC(=O)CC1=CC=CC(C(F)(F)F)=C1 STIMORLKYIPIAQ-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
238000010171 animal model Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
VEQAGSPCZANNDR-UHFFFAOYSA-N azepine-1-sulfonamide Chemical compound NS(=O)(=O)N1C=CC=CC=C1 VEQAGSPCZANNDR-UHFFFAOYSA-N 0.000 description 1
229940125717 barbiturate Drugs 0.000 description 1
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000004424 eye movement Effects 0.000 description 1
239000003925 fat Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
229960002456 hexobarbital Drugs 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000008011 inorganic excipient Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000008012 organic excipient Substances 0.000 description 1
230000010355 oscillation Effects 0.000 description 1
230000000803 paradoxical effect Effects 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
230000028527 righting reflex Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
230000004620 sleep latency Effects 0.000 description 1
230000037322 slow-wave sleep Effects 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
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
230000009154 spontaneous behavior Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000003765 sweetening agent Substances 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
239000001993 wax Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BE154447A 1974-03-20 1975-03-18 Nouveaux thiadiazoles, leur preparation et medicaments les contenant BE826816R (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US45267874A	1974-03-20	1974-03-20

Publications (1)

Publication Number	Publication Date
BE826816R true BE826816R (fr)	1975-09-18

Family

ID=23797453

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE154447A BE826816R (fr)	1974-03-20	1975-03-18	Nouveaux thiadiazoles, leur preparation et medicaments les contenant

Country Status (3)

Country	Link
AT (1)	ATA208775A (de)
BE (1)	BE826816R (de)
ZA (1)	ZA751776B (de)

1975
- 1975-03-18 BE BE154447A patent/BE826816R/fr active
- 1975-03-19 AT AT752087A patent/ATA208775A/de not_active Application Discontinuation
- 1975-03-20 ZA ZA00751776A patent/ZA751776B/xx unknown

Also Published As

Publication number	Publication date
ATA208775A (de)	1979-01-15
ZA751776B (en)	1976-10-27

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