FI66363C - Foerfarande foer framstaellning av 5-merkapto-1,2,3-triazoler - Google Patents

Foerfarande foer framstaellning av 5-merkapto-1,2,3-triazoler Download PDF

Info

Publication number: FI66363C
Authority: FI; Finland
Prior art keywords: formula; mercapto; acid; reaction; thiadiazole
Prior art date: 1978-11-29

Application number

FI793526A

Other languages

English (en)

Finnish (fi)

Other versions

FI793526A (fi

FI66363B (fi

Inventor

Hans-Rudolf Krueger

Original Assignee

Schering Ag

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.)

1978-11-29

Filing date

1979-11-12

Publication date

1984-10-10

1979-11-12 Application filed by Schering Ag filed Critical Schering Ag

1980-05-30 Publication of FI793526A publication Critical patent/FI793526A/fi

1984-06-29 Application granted granted Critical

1984-06-29 Publication of FI66363B publication Critical patent/FI66363B/fi

1984-10-10 Publication of FI66363C publication Critical patent/FI66363C/fi

Links

LLCOQBODWBFTDD-UHFFFAOYSA-N 1h-triazol-1-ium-4-thiolate Chemical class SC1=CNN=N1 LLCOQBODWBFTDD-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
MMVXXBHGORJZQP-UHFFFAOYSA-N thiadiazol-5-ylcarbamic acid Chemical compound OC(=O)NC1=CN=NS1 MMVXXBHGORJZQP-UHFFFAOYSA-N 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 3
UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
238000006555 catalytic reaction Methods 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000003513 alkali Substances 0.000 description 8
238000009835 boiling Methods 0.000 description 7
235000019439 ethyl acetate Nutrition 0.000 description 7
PVGHNTXQMCYYGF-UHFFFAOYSA-N thiadiazol-5-amine Chemical compound NC1=CN=NS1 PVGHNTXQMCYYGF-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
235000002639 sodium chloride Nutrition 0.000 description 6
239000000725 suspension Substances 0.000 description 6
-1 1,2,3-thiadiazole-5-carboxylic acid halides Chemical class 0.000 description 5
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
150000001540 azides Chemical class 0.000 description 5
239000002585 base Substances 0.000 description 5
239000012045 crude solution Substances 0.000 description 5
239000002024 ethyl acetate extract Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
239000007858 starting material Substances 0.000 description 5
FKDUPDCCGBMNPT-UHFFFAOYSA-N 4-methyl-1,2-dihydrotriazole-5-thione Chemical compound CC=1N=NNC=1S FKDUPDCCGBMNPT-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000003377 acid catalyst Substances 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
150000001731 carboxylic acid azides Chemical class 0.000 description 3
238000001035 drying Methods 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
230000007017 scission Effects 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
UDSVLKOSDHNDNJ-UHFFFAOYSA-N thiadiazole-5-carbonyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CN=NS1 UDSVLKOSDHNDNJ-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
OIZCCHUUSZFPIW-UHFFFAOYSA-N 4-methylthiadiazole-5-carbohydrazide Chemical compound CC=1N=NSC=1C(=O)NN OIZCCHUUSZFPIW-UHFFFAOYSA-N 0.000 description 2
238000006088 Dimroth rearrangement reaction Methods 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
ALLQHEFPIVLZCH-UHFFFAOYSA-N phenyl n-(thiadiazol-5-yl)carbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=CN=NS1 ALLQHEFPIVLZCH-UHFFFAOYSA-N 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
GAEVUCDHQSJZEB-UHFFFAOYSA-N tert-butyl n-(4-methylthiadiazol-5-yl)carbamate Chemical compound CC=1N=NSC=1NC(=O)OC(C)(C)C GAEVUCDHQSJZEB-UHFFFAOYSA-N 0.000 description 2
150000003509 tertiary alcohols Chemical class 0.000 description 2
DHTBORBAEQJWLZ-UHFFFAOYSA-N thiadiazole-5-carbohydrazide Chemical class NNC(=O)C1=CN=NS1 DHTBORBAEQJWLZ-UHFFFAOYSA-N 0.000 description 2
BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical class OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
VRDSRXVCRBMZOD-UHFFFAOYSA-N 1-benzyltriazole Chemical compound C1=CN=NN1CC1=CC=CC=C1 VRDSRXVCRBMZOD-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
HXABWNOBBYCXLG-UHFFFAOYSA-N 5-isocyanatothiadiazole Chemical compound O=C=NC1=CN=NS1 HXABWNOBBYCXLG-UHFFFAOYSA-N 0.000 description 1
DGSFDOZBSSGZMW-UHFFFAOYSA-N C(C(C)C)C(=O)CC(C)C.C(C)(=O)OCC Chemical compound C(C(C)C)C(=O)CC(C)C.C(C)(=O)OCC DGSFDOZBSSGZMW-UHFFFAOYSA-N 0.000 description 1
101100124609 Caenorhabditis elegans zyg-12 gene Proteins 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
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 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000010923 batch production Methods 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000029087 digestion Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002641 lithium Chemical group 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000004476 plant protection product Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003852 triazoles Chemical class 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
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
- 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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles

Landscapes

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

FI793526A 1978-11-29 1979-11-12 Foerfarande foer framstaellning av 5-merkapto-1,2,3-triazoler FI66363C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2852067		1978-11-29
DE19782852067 DE2852067A1 (de)	1978-11-29	1978-11-29	Verfahren zur herstellung von 5-mercapto-1,2,3-triazolen

Publications (3)

Publication Number	Publication Date
FI793526A FI793526A (fi)	1980-05-30
FI66363B FI66363B (fi)	1984-06-29
FI66363C true FI66363C (fi)	1984-10-10

Family

ID=6056090

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI793526A FI66363C (fi)	1978-11-29	1979-11-12	Foerfarande foer framstaellning av 5-merkapto-1,2,3-triazoler

Country Status (35)

Country	Link
US (1)	US4259502A (de)
JP (1)	JPS5919942B2 (de)
AR (1)	AR223689A1 (de)
AT (1)	AT371452B (de)
AU (1)	AU532061B2 (de)
BE (1)	BE880340A (de)
BR (1)	BR7907704A (de)
CA (1)	CA1137495A (de)
CH (1)	CH642362A5 (de)
CS (1)	CS209943B2 (de)
DD (1)	DD149521A5 (de)
DE (1)	DE2852067A1 (de)
DK (1)	DK508579A (de)
EG (1)	EG14014A (de)
ES (1)	ES486377A1 (de)
FI (1)	FI66363C (de)
FR (1)	FR2442838A1 (de)
GB (1)	GB2038328B (de)
GR (1)	GR74142B (de)
HU (1)	HU183023B (de)
IE (1)	IE49120B1 (de)
IL (1)	IL58796A0 (de)
IT (1)	IT1127268B (de)
LU (1)	LU81925A1 (de)
MX (1)	MX6016E (de)
NL (1)	NL7908605A (de)
NZ (1)	NZ192180A (de)
PH (1)	PH15774A (de)
PL (1)	PL120299B1 (de)
PT (1)	PT70497A (de)
RO (1)	RO78488A (de)
SE (1)	SE445997B (de)
SU (1)	SU961559A3 (de)
YU (1)	YU41352B (de)
ZA (1)	ZA796479B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2920939A1 (de) *	1979-05-21	1980-11-27	Schering Ag	Verfahren zur herstellung von 5-mercapto-1,2,3-triazolen
DE3139506A1 (de) *	1981-10-01	1983-04-21	Schering Ag, 1000 Berlin Und 4619 Bergkamen	1,2,3-thiadiazol-5-yl-harnstoff-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wuchsregulatorischer und entblaetternder wirkung
US5068347A (en) *	1987-11-23	1991-11-26	Dowelanco	Process for the preparation of 3-mercapto-5-amino-(1h)-1,2,4-triazole

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1476981A (en) *	1974-06-05	1977-06-16	Bristol Myers Co	Substituted penicillanic acids

1978
- 1978-11-29 DE DE19782852067 patent/DE2852067A1/de not_active Withdrawn
1979
- 1979-11-12 FI FI793526A patent/FI66363C/fi not_active IP Right Cessation
- 1979-11-19 YU YU2821/79A patent/YU41352B/xx unknown
- 1979-11-21 US US06/096,574 patent/US4259502A/en not_active Expired - Lifetime
- 1979-11-21 NZ NZ192180A patent/NZ192180A/xx unknown
- 1979-11-23 SE SE7909709A patent/SE445997B/sv unknown
- 1979-11-25 IL IL58796A patent/IL58796A0/xx unknown
- 1979-11-26 LU LU81925A patent/LU81925A1/de unknown
- 1979-11-26 MX MX798498U patent/MX6016E/es unknown
- 1979-11-26 PT PT70497A patent/PT70497A/de unknown
- 1979-11-27 EG EG707/79A patent/EG14014A/xx active
- 1979-11-27 GR GR60618A patent/GR74142B/el unknown
- 1979-11-27 PH PH23335A patent/PH15774A/en unknown
- 1979-11-27 PL PL1979219913A patent/PL120299B1/pl unknown
- 1979-11-27 IT IT27581/79A patent/IT1127268B/it active
- 1979-11-27 ES ES486377A patent/ES486377A1/es not_active Expired
- 1979-11-27 NL NL7908605A patent/NL7908605A/nl not_active Application Discontinuation
- 1979-11-28 AT AT0753579A patent/AT371452B/de not_active IP Right Cessation
- 1979-11-28 AU AU53242/79A patent/AU532061B2/en not_active Ceased
- 1979-11-28 DD DD79217206A patent/DD149521A5/de unknown
- 1979-11-28 HU HU79SCHE703A patent/HU183023B/hu unknown
- 1979-11-28 CA CA000340758A patent/CA1137495A/en not_active Expired
- 1979-11-28 BR BR7907704A patent/BR7907704A/pt unknown
- 1979-11-28 SU SU792845868A patent/SU961559A3/ru active
- 1979-11-29 JP JP54153696A patent/JPS5919942B2/ja not_active Expired
- 1979-11-29 AR AR279068A patent/AR223689A1/es active
- 1979-11-29 BE BE0/198355A patent/BE880340A/fr not_active IP Right Cessation
- 1979-11-29 CH CH1062679A patent/CH642362A5/de not_active IP Right Cessation
- 1979-11-29 FR FR7929392A patent/FR2442838A1/fr active Granted
- 1979-11-29 RO RO7999390A patent/RO78488A/ro unknown
- 1979-11-29 ZA ZA00796479A patent/ZA796479B/xx unknown
- 1979-11-29 CS CS798246A patent/CS209943B2/cs unknown
- 1979-11-29 IE IE2291/79A patent/IE49120B1/en unknown
- 1979-11-29 GB GB7941230A patent/GB2038328B/en not_active Expired
- 1979-11-29 DK DK508579A patent/DK508579A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
GB2038328B (en)	1983-03-23
PL219913A1 (de)	1980-12-01
AR223689A1 (es)	1981-09-15
EG14014A (en)	1982-09-30
FR2442838A1 (fr)	1980-06-27
SU961559A3 (ru)	1982-09-23
AU532061B2 (en)	1983-09-15
IL58796A0 (en)	1980-02-29
ES486377A1 (es)	1980-05-16
YU282179A (en)	1983-02-28
FR2442838B1 (de)	1983-10-21
ATA753579A (de)	1982-11-15
IT1127268B (it)	1986-05-21
AU5324279A (en)	1980-06-26
IE49120B1 (en)	1985-08-07
IT7927581A0 (it)	1979-11-27
FI793526A (fi)	1980-05-30
US4259502A (en)	1981-03-31
CS209943B2 (en)	1981-12-31
IE792291L (en)	1980-05-29
LU81925A1 (de)	1980-02-29
PL120299B1 (en)	1982-02-27
RO78488A (ro)	1982-02-26
BE880340A (fr)	1980-05-29
DD149521A5 (de)	1981-07-15
AT371452B (de)	1983-06-27
ZA796479B (en)	1980-11-26
GB2038328A (en)	1980-07-23
GR74142B (de)	1984-06-06
BR7907704A (pt)	1980-07-22
PH15774A (en)	1983-03-24
HU183023B (en)	1984-04-28
MX6016E (es)	1984-09-24
FI66363B (fi)	1984-06-29
NL7908605A (nl)	1980-06-02
SE445997B (sv)	1986-08-04
SE7909709L (sv)	1980-05-30
JPS5919942B2 (ja)	1984-05-09
DK508579A (da)	1980-05-30
DE2852067A1 (de)	1980-06-12
CA1137495A (en)	1982-12-14
YU41352B (en)	1987-02-28
NZ192180A (en)	1982-11-23
PT70497A (de)	1979-12-01
CH642362A5 (de)	1984-04-13
JPS5573664A (en)	1980-06-03

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: SCHERING AKTIENGESELLSCHAFT

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