CH616161A5 - - Google Patents

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Info

Publication number: CH616161A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; het; general formula; temperature; pyridazinyl
Prior art date: 1976-02-10

Application number

CH158177A

Other languages

English (en)

French (fr)

Inventor

Michel Barreau

Claude Cotrel

Claude Jeanmart

Original Assignee

Rhone Poulenc Ind

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.)

1976-02-10

Filing date

1977-02-09

Publication date

1980-03-14

1976-02-10 Priority claimed from FR7603603A external-priority patent/FR2340736A1/fr

1976-11-30 Priority claimed from FR7636038A external-priority patent/FR2371925A1/fr

1977-02-09 Application filed by Rhone Poulenc Ind filed Critical Rhone Poulenc Ind

1980-03-14 Publication of CH616161A5 publication Critical patent/CH616161A5/fr

Links

YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 60
125000004432 carbon atom Chemical group C* 0.000 claims description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
150000002391 heterocyclic compounds Chemical class 0.000 claims description 13
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical group 0.000 claims description 5
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
239000008096 xylene Substances 0.000 claims description 3
150000003738 xylenes Chemical class 0.000 claims description 3
PCGDBWLKAYKBTN-UHFFFAOYSA-N 1,2-dithiole Chemical class C1SSC=C1 PCGDBWLKAYKBTN-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
239000011574 phosphorus Substances 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
239000000725 suspension Substances 0.000 description 20
239000012153 distilled water Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000008346 aqueous phase Substances 0.000 description 16
239000000243 solution Substances 0.000 description 16
239000000047 product Substances 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000010908 decantation Methods 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
238000001816 cooling Methods 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
238000001914 filtration Methods 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 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 11
239000000203 mixture Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
238000010992 reflux Methods 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
239000002198 insoluble material Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
-1 (3-pyridazinyl) -3-oxo-propionate Chemical compound 0.000 description 4
KBKWNTXKUFAICC-UHFFFAOYSA-N 6-(dimethylamino)pyridazine-3-carbonitrile Chemical compound CN(C)C1=CC=C(C#N)N=N1 KBKWNTXKUFAICC-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
UQIRZEDQNZFQNP-UHFFFAOYSA-N 1-[6-(dimethylamino)pyridazin-3-yl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)N=N1 UQIRZEDQNZFQNP-UHFFFAOYSA-N 0.000 description 3
CNJMBLXXACEVSU-UHFFFAOYSA-N 6-iodo-n,n-dimethylpyridazin-3-amine Chemical compound CN(C)C1=CC=C(I)N=N1 CNJMBLXXACEVSU-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
SJWGLCDFBFCHNV-UHFFFAOYSA-N 6-methylpyridazine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)N=N1 SJWGLCDFBFCHNV-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
231100000111 LD50 Toxicity 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
XUVKQXXTTMEDIS-UHFFFAOYSA-N N1=NC(=CC=C1)C(C(=O)OCC)C=O Chemical compound N1=NC(=CC=C1)C(C(=O)OCC)C=O XUVKQXXTTMEDIS-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
GCLHXKPPHRIJOE-UHFFFAOYSA-N 3,6-diiodopyridazine Chemical compound IC1=CC=C(I)N=N1 GCLHXKPPHRIJOE-UHFFFAOYSA-N 0.000 description 1
OAKURXIZZOAYBC-UHFFFAOYSA-N 3-oxopropanoic acid Chemical compound OC(=O)CC=O OAKURXIZZOAYBC-UHFFFAOYSA-N 0.000 description 1
MBVKWGKPRADLAP-UHFFFAOYSA-N 6-methylpyridazine-3-carbonitrile Chemical compound CC1=CC=C(C#N)N=N1 MBVKWGKPRADLAP-UHFFFAOYSA-N 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
238000003512 Claisen condensation reaction Methods 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
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 1
241000242680 Schistosoma mansoni Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
235000012538 ammonium bicarbonate Nutrition 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
244000309464 bull Species 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
OQCZRDWKZXSHGS-ZHZULCJRSA-N ethyl (2z)-2-[(2-acetyloxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5h-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate Chemical compound O=C1N2C(C=3C=CC=CC=3)C(C(=O)OCC)=C(C)N=C2S\C1=C/C1=CC=CC=C1OC(C)=O OQCZRDWKZXSHGS-ZHZULCJRSA-N 0.000 description 1
GTKICVKNDVGKCV-UHFFFAOYSA-N ethyl 6-(dimethylamino)pyridazine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(N(C)C)N=N1 GTKICVKNDVGKCV-UHFFFAOYSA-N 0.000 description 1
GNCUVFPHYFZIRH-UHFFFAOYSA-N ethyl 6-methylpyridazine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(C)N=N1 GNCUVFPHYFZIRH-UHFFFAOYSA-N 0.000 description 1
LLLVOBWNRQYTKR-UHFFFAOYSA-N ethyl pyridazine-3-carboxylate Chemical compound CCOC(=O)C1=CC=CN=N1 LLLVOBWNRQYTKR-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
GXZQHMHLHHUHAM-UHFFFAOYSA-N methyl pyrimidine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=N1 GXZQHMHLHHUHAM-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000000053 physical method Methods 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
WUYDVXGCTKVALO-UHFFFAOYSA-N pyridazin-3-yl propanoate Chemical compound CCC(=O)OC1=CC=CN=N1 WUYDVXGCTKVALO-UHFFFAOYSA-N 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics

Landscapes

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

CH158177A 1976-02-10 1977-02-09 CH616161A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7603603A FR2340736A1 (fr)	1976-02-10	1976-02-10	Nouveaux derives du dithiole-1,2, leur preparation et les compositions qui les contiennent
FR7636038A FR2371925A1 (fr)	1976-11-30	1976-11-30	Nouveaux derives du dithiole-1,2, leur preparation et les compositions qui les contiennent

Publications (1)

Publication Number	Publication Date
CH616161A5 true CH616161A5 (de)	1980-03-14

Family

ID=26219292

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH158177A CH616161A5 (de)	1976-02-10	1977-02-09

Country Status (22)

Country	Link
US (1)	US4104386A (de)
JP (1)	JPS52105181A (de)
AR (1)	AR220892A1 (de)
AT (2)	AT349028B (de)
AU (1)	AU505778B2 (de)
CA (1)	CA1075239A (de)
CH (1)	CH616161A5 (de)
DE (1)	DE2705582C3 (de)
DK (1)	DK55677A (de)
EG (1)	EG13192A (de)
ES (1)	ES458019A1 (de)
GB (1)	GB1520231A (de)
HU (1)	HU172527B (de)
IE (1)	IE44462B1 (de)
IL (1)	IL51402A (de)
LU (1)	LU76727A1 (de)
NL (1)	NL175823C (de)
OA (1)	OA05566A (de)
PH (1)	PH12622A (de)
PT (1)	PT66174B (de)
SE (1)	SE427273B (de)
SU (1)	SU837324A3 (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1454910A1 (de)	2003-03-07	2004-09-08	Sanofi-Synthelabo	Substitutierte Pyrimidinyl-2-(diaza-bicyclo-alkyl)-pyrimidonederivate
TW200740779A (en)	2005-07-22	2007-11-01	Mitsubishi Pharma Corp	Intermediate compound for synthesizing pharmaceutical agent and production method thereof
EP1939187A1 (de)	2006-12-20	2008-07-02	Sanofi-Aventis	Substituierte Heteroaryl-Pyridopyrimidon-Derivate
EP2085400A1 (de) *	2008-01-29	2009-08-05	Sanofi-Aventis	Substituierte Heteroarylamid-Oxazepinopyrimidon-Derivate
EP2090578A1 (de)	2008-01-29	2009-08-19	Sanofi-Aventis	Substituierte Arylamid-Diazepinopyrimidon-Derivate zur Behandlung von neurodegenerativen Erkrankungen verursacht durch eine abnormale GSK3-beta-Aktivität
EP2090579A1 (de)	2008-01-29	2009-08-19	Sanofi-Aventis	Substituierte Heteroarylamiddiazepinopyrimidon-Derivate
EP2085399A1 (de) *	2008-01-29	2009-08-05	Sanofi-Aventis	Substituierte Arylamidoxazepinopyrimidon-Derivate
EP2138495A1 (de) *	2008-06-26	2009-12-30	sanofi-aventis	Substituierte Pyrimido[2,1-a]isochinolin-4-on-Derivate
EP2138488A1 (de) *	2008-06-26	2009-12-30	sanofi-aventis	4-(Pyridin-4-yl)-1H-[1,3,5]Triazin-2-one-Verbindungen als GSK3-beta Hemmer zur Behandlung neurodegenerative Erkrankungen
EP2138485A1 (de) *	2008-06-26	2009-12-30	sanofi-aventis	Substituierte N-Oxid-Pyrazin-Derivate
EP2138493A1 (de) *	2008-06-26	2009-12-30	Sanofi-Aventis	Substituierte Pyrimidon-Derivate
EP2138498A1 (de) *	2008-06-26	2009-12-30	sanofi-aventis	Substituierte trizyklische Derivate gegen neurodegenerative Erkrankungen
EP2138494A1 (de) *	2008-06-26	2009-12-30	Sanofi-Aventis	Substituierte Alkylpyrimidin-4-one-Derivate
EP2138492A1 (de)	2008-06-26	2009-12-30	Sanofi-Aventis	Substituierte Pyrimidin-4-one-Derivate
CN109776489B (zh) *	2019-02-26	2021-03-30	温州大学	铜催化苯丙炔胺硫环化合成1,2-二硫-3-硫酮衍生物的方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1526768A (fr)	1963-01-16	1968-05-31		Procédé de préparation de dérivés sulfoniques de dithiole-1, 2 thiones-3 diversement substituées, et applications des produits ainsi obtenus
US3957925A (en) *	1971-07-22	1976-05-18	Petrolite Corporation	Thiophosphates
US3791789A (en) *	1972-06-22	1974-02-12	Petrolite Corp	1,2-dithiolium compounds as corrosion inhibitors

1977
- 1977-02-01 EG EG60/77A patent/EG13192A/xx active
- 1977-02-02 NL NLAANVRAGE7701103,A patent/NL175823C/xx not_active IP Right Cessation
- 1977-02-08 IL IL51402A patent/IL51402A/xx unknown
- 1977-02-08 HU HU77RO00000913A patent/HU172527B/hu unknown
- 1977-02-08 AR AR266483A patent/AR220892A1/es active
- 1977-02-09 AU AU22139/77A patent/AU505778B2/en not_active Expired
- 1977-02-09 LU LU76727A patent/LU76727A1/xx unknown
- 1977-02-09 PH PH19437A patent/PH12622A/en unknown
- 1977-02-09 GB GB5368/77A patent/GB1520231A/en not_active Expired
- 1977-02-09 PT PT66174A patent/PT66174B/pt unknown
- 1977-02-09 JP JP1347177A patent/JPS52105181A/ja active Granted
- 1977-02-09 US US05/766,967 patent/US4104386A/en not_active Expired - Lifetime
- 1977-02-09 SE SE7701459A patent/SE427273B/xx unknown
- 1977-02-09 IE IE269/77A patent/IE44462B1/en unknown
- 1977-02-09 CA CA271,430A patent/CA1075239A/en not_active Expired
- 1977-02-09 CH CH158177A patent/CH616161A5/fr not_active IP Right Cessation
- 1977-02-09 DK DK55677A patent/DK55677A/da not_active Application Discontinuation
- 1977-02-10 AT AT90177A patent/AT349028B/de not_active IP Right Cessation
- 1977-02-10 DE DE2705582A patent/DE2705582C3/de not_active Expired
- 1977-02-10 SU SU772450452A patent/SU837324A3/ru active
- 1977-02-10 OA OA56068A patent/OA05566A/xx unknown
- 1977-04-21 ES ES458019A patent/ES458019A1/es not_active Expired
1978
- 1978-02-02 AT AT71978A patent/AT349029B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
NL175823C (nl)	1985-01-02
AU505778B2 (en)	1979-11-29
SU837324A3 (ru)	1981-06-07
NL7701103A (nl)	1977-08-12
PH12622A (en)	1979-07-05
DE2705582C3 (de)	1981-09-24
IL51402A0 (en)	1977-04-29
AT349028B (de)	1979-03-12
PT66174A (fr)	1977-03-01
PT66174B (fr)	1978-07-10
DE2705582B2 (de)	1980-08-21
LU76727A1 (de)	1977-08-18
JPS625912B2 (de)	1987-02-07
HU172527B (hu)	1978-09-28
NL175823B (nl)	1984-08-01
AU2213977A (en)	1978-08-17
CA1075239A (en)	1980-04-08
US4104386A (en)	1978-08-01
AT349029B (de)	1979-03-12
DK55677A (da)	1977-08-11
IL51402A (en)	1980-07-31
SE427273B (sv)	1983-03-21
OA05566A (fr)	1981-04-30
ATA90177A (de)	1978-08-15
EG13192A (en)	1982-12-31
SE7701459L (sv)	1977-08-11
AR220892A1 (es)	1980-12-15
IE44462L (en)	1977-08-10
GB1520231A (en)	1978-08-02
DE2705582A1 (de)	1977-08-11
JPS52105181A (en)	1977-09-03
ATA71978A (de)	1978-08-15
ES458019A1 (es)	1978-08-16
IE44462B1 (en)	1981-12-02

Legal Events

Date	Code	Title	Description
1991-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0001534B1 (de)	1981-08-12	Pyrrolderivate, Verfahren zu ihrer Herstellung und ihre therapeutischen Verwendungen
CA1073906A (fr)	1980-03-18	Derives du dithiole-1,2, leur preparation et les compositions qui les contiennent
CA1075239A (en)	1980-04-08	1,2-dithiol derivatives, methods of preparation, compositions thereof
FR2472564A1 (fr)	1981-07-03	Nouveaux aryl-1 arylsulfonyl-4 1h-pyrazolols-3, et procede pour les preparer
FR2621038A1 (fr)	1989-03-31	Derives d'alcadienes, leurs preparations, les medicaments les contenant et produits intermediaires
EP0000453B1 (de)	1980-07-23	Verfahren zur Herstellung von Thienopyridinderivaten.
BE779775A (fr)	1972-08-24	Derives de l'uree, procede pour les preparer et leurs applications
EP0294258A1 (de)	1988-12-07	Hydrazin-Derivate, Verfahren zu deren Erhaltung und diese enthaltende pharmazeutische Zusammensetzungen
EP0045251B1 (de)	1983-11-30	Thiazolo(3,2-a)pyrimidinderivate, ihre Herstellung und Arzneimittel, die diese Derivate enthalten
EP0502020B1 (de)	1994-01-26	BENZO[b]PHENANTHROLINDERIVATE, IHRE HERSTELLUNG UND IHRE THERAPEUTISCHE VERWENDUNG
EP0017523B1 (de)	1982-09-01	Derivate des Dithiepinno (1,4)(2,3-c) pyrrols, ihre Herstellung und sie enthaltende Medikamente
CH594650A5 (en)	1978-01-13	Antiinflammatory (1,2)-benzothiazine derivs. prepn.
CH392483A (fr)	1965-05-31	Procédé de préparation de nouveaux esters d'acides 4-halo-3-sulfamoyl-benzoïques
CA1197511A (fr)	1985-12-03	Haloalkyl-8-4h-¬1\|-benzopyran-4-ones, et procede de preparation
BE884977A (fr)	1981-03-02	Nouveau n-phenyl-benzamides utiles dans le traitement de l'inflammation et de la douleur des mammiferes
EP0002401A1 (de)	1979-06-13	Naphtalen-Derivate, Verfahren zu deren Herstellung und deren Verwendung in der Therapeutik
BE563113A (de)
EP0097550B1 (de)	1986-01-15	Verfahren zur Herstellung von Cystamin-Derivaten mit onkostatischer Wirkung
FR2633622A1 (fr)	1990-01-05	Derives de sulfonyl indolizine, leur procede de preparation et leur utilisation comme intermediaires de synthese
CH619464A5 (en)	1980-09-30	Process for the preparation of new 1,2-dithiole derivatives
CA1134360A (fr)	1982-10-26	Derives de l'isoquinoleine, leur preparation et les compositions qui les contiennent
EP0100257A2 (de)	1984-02-08	Aminoalkylnaphthalen-Derivate, ihre Salze und Verfahren zu ihrer Herstellung und die Verwendung dieser Derivate und Salze in der Therapeutik
CH617935A5 (en)	1980-06-30	Preparation of new isoindoline derivatives
CH615926A5 (en)	1980-02-29	Process for the preparation of new derivatives of 1,2-dithiole
EP0188150A1 (de)	1986-07-23	Verfahren zur Herstellung von optischen Isomeren von Thiazolo[3,2-a]pyrimidinen, Isomere, diese enthaltende pharmazeutische Zubereitungen und Zwischenprodukte in dieser Herstellung