CS203932B2 - Process for prepating new derivatives of thiazoline - Google Patents

Process for prepating new derivatives of thiazoline Download PDF

Info

Publication number: CS203932B2
Authority: CS; Czechoslovakia
Prior art keywords: methyl; pyridyl; alkyl; hydrogen; solution
Prior art date: 1977-10-19

Application number

CS786806A

Other languages

Czech (cs)

English (en)

Inventor

Jean-Dominique Bourzat

Daniel Fargo

Andre Leger

Gerard Ponsinet

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.)

1977-10-19

Filing date

1978-10-19

Publication date

1981-03-31

1977-10-19 Priority claimed from FR7731431A external-priority patent/FR2406637A1/fr

1978-09-13 Priority claimed from FR7826304A external-priority patent/FR2436148A1/fr

1978-10-19 Application filed by Rhone Poulenc Ind filed Critical Rhone Poulenc Ind

1981-03-31 Publication of CS203932B2 publication Critical patent/CS203932B2/cs

Links

238000000034 method Methods 0.000 title claims description 35
150000003549 thiazolines Chemical class 0.000 title claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
230000018044 dehydration Effects 0.000 claims description 10
238000006297 dehydration reaction Methods 0.000 claims description 10
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims description 3
125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 31
238000009835 boiling Methods 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
-1 alkyl radicals Chemical class 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
238000001953 recrystallisation Methods 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000012153 distilled water Substances 0.000 description 15
238000001914 filtration Methods 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 12
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
150000001875 compounds Chemical class 0.000 description 11
238000010992 reflux Methods 0.000 description 11
HVOMZNUEIIDPOH-UHFFFAOYSA-N 1,3-thiazole-4-thione Chemical compound S=C1CSC=N1 HVOMZNUEIIDPOH-UHFFFAOYSA-N 0.000 description 10
239000012990 dithiocarbamate Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 9
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000000047 product Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
JLCZWDGDDGMLHA-UHFFFAOYSA-N 1-chloro-3-methoxypropan-2-one Chemical compound COCC(=O)CCl JLCZWDGDDGMLHA-UHFFFAOYSA-N 0.000 description 2
QVMRSFQXWJGXRL-UHFFFAOYSA-N 1-chloro-4-methylpentan-2-one Chemical compound CC(C)CC(=O)CCl QVMRSFQXWJGXRL-UHFFFAOYSA-N 0.000 description 2
OYJGEOAXBALSMM-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole Chemical compound C1NC=CS1 OYJGEOAXBALSMM-UHFFFAOYSA-N 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
KCPACMFMDRACBZ-UHFFFAOYSA-N 4-butyl-4-hydroxy-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CCCCC1(O)CSC(=S)N1C1=CC=CC(C)=N1 KCPACMFMDRACBZ-UHFFFAOYSA-N 0.000 description 2
YDIPFFIZYCBPKD-UHFFFAOYSA-N 4-cyclopropyl-4-hydroxy-3-pyridin-2-yl-1,3-thiazolidine-2-thione Chemical compound C1CC1C1(O)CSC(=S)N1C1=CC=CC=N1 YDIPFFIZYCBPKD-UHFFFAOYSA-N 0.000 description 2
MJMMSGUOLKDZSW-UHFFFAOYSA-N 4-hydroxy-4-(methoxymethyl)-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound COCC1(O)CSC(=S)N1C1=CC=CC(C)=N1 MJMMSGUOLKDZSW-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
MJNPQGVYFZGKQW-UHFFFAOYSA-N (6-methylpyridin-2-yl) carbamodithioate Chemical compound C(N)(SC1=NC(=CC=C1)C)=S MJNPQGVYFZGKQW-UHFFFAOYSA-N 0.000 description 1
YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
AALRHBLMAVGWRR-UHFFFAOYSA-N 1-chlorobutan-2-one Chemical compound CCC(=O)CCl AALRHBLMAVGWRR-UHFFFAOYSA-N 0.000 description 1
ZXWAHROJUXWVCU-UHFFFAOYSA-N 2-chloro-1-cyclopropylethanone Chemical compound ClCC(=O)C1CC1 ZXWAHROJUXWVCU-UHFFFAOYSA-N 0.000 description 1
QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
FKAXLEKRJSNZCF-UHFFFAOYSA-N 3-(6-ethylpyridin-2-yl)-4-hydroxy-4-methyl-1,3-thiazolidine-2-thione Chemical compound CCC1=CC=CC(N2C(CSC2=S)(C)O)=N1 FKAXLEKRJSNZCF-UHFFFAOYSA-N 0.000 description 1
OIMRLHCSLQUXLL-UHFFFAOYSA-N 3-chlorobutan-2-one Chemical compound CC(Cl)C(C)=O OIMRLHCSLQUXLL-UHFFFAOYSA-N 0.000 description 1
OEPZZBQQOWWJIB-UHFFFAOYSA-N 4-ethyl-3-(6-ethylpyridin-2-yl)-4-hydroxy-1,3-thiazolidine-2-thione Chemical compound CCC1=CC=CC(N2C(CSC2=S)(O)CC)=N1 OEPZZBQQOWWJIB-UHFFFAOYSA-N 0.000 description 1
SYYBGRAWXXXMMP-UHFFFAOYSA-N 4-hydroxy-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CC1=CC=CC(N2C(SCC2O)=S)=N1 SYYBGRAWXXXMMP-UHFFFAOYSA-N 0.000 description 1
PJZZQJBZVPODLJ-UHFFFAOYSA-N 4-hydroxy-4,5-dimethyl-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CC1(O)C(C)SC(=S)N1C1=CC=CC(C)=N1 PJZZQJBZVPODLJ-UHFFFAOYSA-N 0.000 description 1
JMFDWHRKNVBBKX-UHFFFAOYSA-N 4-hydroxy-4-methyl-3-(4-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CC1=CC=NC(N2C(CSC2=S)(C)O)=C1 JMFDWHRKNVBBKX-UHFFFAOYSA-N 0.000 description 1
WTPRNYOTYMMEGB-UHFFFAOYSA-N 4-hydroxy-4-methyl-3-(6-propylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CCCC1=CC=CC(N2C(CSC2=S)(C)O)=N1 WTPRNYOTYMMEGB-UHFFFAOYSA-N 0.000 description 1
JDRTXRTVJTWITJ-UHFFFAOYSA-N 6-propylpyridin-2-amine Chemical compound CCCC1=CC=CC(N)=N1 JDRTXRTVJTWITJ-UHFFFAOYSA-N 0.000 description 1
FJNJDGVJWCIUFW-UHFFFAOYSA-N 6-propylpyridine Chemical compound CCCC1=C=CC=C[N]1 FJNJDGVJWCIUFW-UHFFFAOYSA-N 0.000 description 1
BEGGKYJGVPGIES-UHFFFAOYSA-N C(N)(SC1=NC=CC=C1)=S.C(C)N(CC)CC Chemical compound C(N)(SC1=NC=CC=C1)=S.C(C)N(CC)CC BEGGKYJGVPGIES-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229940123464 Thiazolidinedione Drugs 0.000 description 1
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
ZERJVEQLQZTTQS-UHFFFAOYSA-N n,n-diethylethanamine;pyridin-2-ylcarbamodithioic acid Chemical compound CCN(CC)CC.SC(=S)NC1=CC=CC=N1 ZERJVEQLQZTTQS-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (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)

CS786806A 1977-10-19 1978-10-19 Process for prepating new derivatives of thiazoline CS203932B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7731431A FR2406637A1 (fr)	1977-10-19	1977-10-19	Nouveaux derives de la thiazoline, leur preparation et les compositions pharmaceutiques qui les contiennent
FR7826304A FR2436148A1 (fr)	1978-09-13	1978-09-13	Nouveaux derives de la thiazoline, leur preparation et les medicaments qui les contiennent

Publications (1)

Publication Number	Publication Date
CS203932B2 true CS203932B2 (en)	1981-03-31

Family

ID=26220267

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS786806A CS203932B2 (en)	1977-10-19	1978-10-19	Process for prepating new derivatives of thiazoline

Country Status (22)

Country	Link
US (1)	US4167571A (fr)
JP (1)	JPS5479285A (fr)
AT (1)	ATA750578A (fr)
AU (1)	AU4078678A (fr)
CA (1)	CA1098906A (fr)
CS (1)	CS203932B2 (fr)
DE (1)	DE2845624A1 (fr)
DK (1)	DK464378A (fr)
ES (1)	ES474350A1 (fr)
FI (1)	FI783184A7 (fr)
GB (1)	GB2006210A (fr)
GR (1)	GR64044B (fr)
HU (1)	HU175528B (fr)
IL (1)	IL55757A0 (fr)
IT (1)	IT1101658B (fr)
LU (1)	LU80389A1 (fr)
NL (1)	NL7810230A (fr)
NO (1)	NO783529L (fr)
NZ (1)	NZ188676A (fr)
PT (1)	PT68668A (fr)
SE (1)	SE7810864L (fr)
SU (1)	SU793398A3 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2464954A2 (fr) *	1979-09-12	1981-03-20	Rhone Poulenc Ind	Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent
NL9001162A (nl) *	1990-05-18	1991-12-16	Stamicarbon	Werkwijze ter bereiding van 2-n-acylaminopyridines en 2-aminopyridines uit 5-oxoalkaannitriloximmen alsmede deze 5-oxoalkaannitriloximmen, 2-n-acylaminopyridines en 2-aminopyridines.
CN102234271B (zh) *	2010-04-21	2015-06-10	北京大学	芳杂(烷基)氨基二硫代甲酸酯类化合物、其制备方法和应用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3761485A (en) *	1971-09-07	1973-09-25	Parke Davis & Co	3-(5-chloro-2-pyridyl)rhodanine and 3-(5-chloro-2-pyridyl)-5-(lower alkyl)rhodanines

1978
- 1978-10-11 NL NL7810230A patent/NL7810230A/xx not_active Application Discontinuation
- 1978-10-17 NZ NZ188676A patent/NZ188676A/xx unknown
- 1978-10-17 AU AU40786/78A patent/AU4078678A/en active Pending
- 1978-10-17 GR GR57454A patent/GR64044B/el unknown
- 1978-10-17 US US05/952,198 patent/US4167571A/en not_active Expired - Lifetime
- 1978-10-17 GB GB7840801A patent/GB2006210A/en not_active Withdrawn
- 1978-10-17 JP JP12691678A patent/JPS5479285A/ja active Pending
- 1978-10-18 DK DK464378A patent/DK464378A/da unknown
- 1978-10-18 CA CA313,694A patent/CA1098906A/fr not_active Expired
- 1978-10-18 SU SU782674199A patent/SU793398A3/ru active
- 1978-10-18 NO NO783529A patent/NO783529L/no unknown
- 1978-10-18 LU LU80389A patent/LU80389A1/fr unknown
- 1978-10-18 PT PT68668A patent/PT68668A/fr unknown
- 1978-10-18 IL IL7855757A patent/IL55757A0/xx unknown
- 1978-10-18 SE SE7810864A patent/SE7810864L/xx unknown
- 1978-10-19 ES ES474350A patent/ES474350A1/es not_active Expired
- 1978-10-19 DE DE19782845624 patent/DE2845624A1/de not_active Ceased
- 1978-10-19 CS CS786806A patent/CS203932B2/cs unknown
- 1978-10-19 AT AT0750578A patent/ATA750578A/de not_active Application Discontinuation
- 1978-10-19 HU HU78RO996A patent/HU175528B/hu unknown
- 1978-10-19 FI FI783184A patent/FI783184A7/fi unknown
- 1978-10-19 IT IT28911/78A patent/IT1101658B/it active

Also Published As

Publication number	Publication date
NZ188676A (en)	1980-10-24
HU175528B (hu)	1980-08-28
GR64044B (en)	1980-01-19
JPS5479285A (en)	1979-06-25
DK464378A (da)	1979-04-20
LU80389A1 (fr)	1979-06-15
CA1098906A (fr)	1981-04-07
FI783184A7 (fi)	1979-04-20
AU4078678A (en)	1980-04-24
IT7828911A0 (it)	1978-10-19
PT68668A (fr)	1978-11-01
NL7810230A (nl)	1979-04-23
ATA750578A (de)	1981-07-15
US4167571A (en)	1979-09-11
GB2006210A (en)	1979-05-02
IL55757A0 (en)	1978-12-17
NO783529L (no)	1979-04-20
ES474350A1 (es)	1979-04-16
DE2845624A1 (de)	1979-04-26
SU793398A3 (ru)	1980-12-30
SE7810864L (sv)	1979-04-20
IT1101658B (it)	1985-10-07

Publication	Publication Date	Title
EP0154190A1 (fr)	1985-09-11	Pyridones
CH617433A5 (fr)	1980-05-30
EP0266558A2 (fr)	1988-05-11	5-Alkylbenzimidazoles, leur procédé de préparation et médicaments les contenant
US3455924A (en)	1969-07-15	Dianisylimidazoles
US3847921A (en)	1974-11-12	Pharmacologically active 3-piperazinyl-carbonyloxy-2-pyridyl-isoindolin-1-ones
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