SU643083A3 - Способ получени производных 1,4-дифенил-3-пиразолин-5-она - Google Patents

Способ получени производных 1,4-дифенил-3-пиразолин-5-она

Info

Publication number: SU643083A3
Authority: SU; USSR - Soviet Union
Prior art keywords: pyrazolin; ethyl; mixture; trifluoro; bromine
Prior art date: 1975-12-11

Application number

SU762427094A

Other languages

English (en)

Russian (ru)

Inventor

Ричард Бек Джеймс

Питер Гайевски Роберт

Original Assignee

Эли Лилли Энд Компани (Фирма)

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.)

1975-12-11

Filing date

1976-12-10

Publication date

1979-01-15

1976-09-20 Priority claimed from US05/724,502 external-priority patent/US4075003A/en

1976-12-10 Application filed by Эли Лилли Энд Компани (Фирма) filed Critical Эли Лилли Энд Компани (Фирма)

1979-01-15 Application granted granted Critical

1979-01-15 Publication of SU643083A3 publication Critical patent/SU643083A3/ru

Links

238000000034 method Methods 0.000 title claims 2
239000000203 mixture Substances 0.000 claims description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
238000010992 reflux Methods 0.000 claims description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 8
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
-1 atropic acid methyl ester Chemical class 0.000 claims description 3
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
229910052794 bromium Inorganic materials 0.000 claims 5
229910052801 chlorine Inorganic materials 0.000 claims 5
239000000460 chlorine Substances 0.000 claims 5
239000001257 hydrogen Substances 0.000 claims 5
229910052739 hydrogen Inorganic materials 0.000 claims 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
229910052731 fluorine Inorganic materials 0.000 claims 3
239000011737 fluorine Substances 0.000 claims 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
XNWYPYFQYFUUTE-UHFFFAOYSA-N 2,4-diphenyl-1h-pyrazol-3-one Chemical class O=C1C(C=2C=CC=CC=2)=CNN1C1=CC=CC=C1 XNWYPYFQYFUUTE-UHFFFAOYSA-N 0.000 claims 1
ALADYIMHFLKYME-UHFFFAOYSA-N 2-(3-chlorophenyl)-1-ethyl-4-phenylpyrazol-3-one Chemical compound O=C1N(C=2C=C(Cl)C=CC=2)N(CC)C=C1C1=CC=CC=C1 ALADYIMHFLKYME-UHFFFAOYSA-N 0.000 claims 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
239000002168 alkylating agent Substances 0.000 claims 1
229940100198 alkylating agent Drugs 0.000 claims 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
150000008050 dialkyl sulfates Chemical class 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
150000002391 heterocyclic compounds Chemical class 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
238000001228 spectrum Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 7
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 5
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
229940067157 phenylhydrazine Drugs 0.000 description 3
239000002904 solvent Substances 0.000 description 3
CRRIAWUJYMLJOE-UHFFFAOYSA-N (3-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(Cl)=C1 CRRIAWUJYMLJOE-UHFFFAOYSA-N 0.000 description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
XLIWHBWGBRQLQH-UHFFFAOYSA-N methyl 2-(3-chlorophenyl)prop-2-enoate Chemical compound COC(=O)C(=C)C1=CC=CC(Cl)=C1 XLIWHBWGBRQLQH-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
PESJTQQZJJTNOC-UHFFFAOYSA-N (3-bromophenyl)hydrazine Chemical compound NNC1=CC=CC(Br)=C1 PESJTQQZJJTNOC-UHFFFAOYSA-N 0.000 description 1
SKVGLOFWEJFQKU-UHFFFAOYSA-N (3-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(F)=C1 SKVGLOFWEJFQKU-UHFFFAOYSA-N 0.000 description 1
KBRQEEHDWOQDES-UHFFFAOYSA-N 2,4-bis(3-chlorophenyl)-1-ethylpyrazol-3-one Chemical compound O=C1N(C=2C=C(Cl)C=CC=2)N(CC)C=C1C1=CC=CC(Cl)=C1 KBRQEEHDWOQDES-UHFFFAOYSA-N 0.000 description 1
LSRUOHOVDCISNX-UHFFFAOYSA-N 2,4-bis(3-chlorophenyl)-1h-pyrazol-3-one Chemical compound ClC1=CC=CC(C=2C(N(C=3C=C(Cl)C=CC=3)NC=2)=O)=C1 LSRUOHOVDCISNX-UHFFFAOYSA-N 0.000 description 1
NQVCUTTYKIQMGZ-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-phenyl-1h-pyrazol-3-one Chemical compound ClC1=CC=CC(N2C(C(C=3C=CC=CC=3)=CN2)=O)=C1 NQVCUTTYKIQMGZ-UHFFFAOYSA-N 0.000 description 1
GNRYQWDSNNTICP-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-pyrazol-3-one Chemical compound FC1=CC=CC(N2C(C=CN2)=O)=C1 GNRYQWDSNNTICP-UHFFFAOYSA-N 0.000 description 1
ADODRSVGNHNKAT-UHFFFAOYSA-N 2-Chlorophenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1Cl ADODRSVGNHNKAT-UHFFFAOYSA-N 0.000 description 1
QRXXROXHMWWNGU-UHFFFAOYSA-N 4-(3-chlorophenyl)-1-methyl-2-phenylpyrazol-3-one Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C=C1C1=CC=CC(Cl)=C1 QRXXROXHMWWNGU-UHFFFAOYSA-N 0.000 description 1
HOWAWNVFEFCJAO-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-phenyl-1h-pyrazol-3-one Chemical compound ClC1=CC=CC(C=2C(N(C=3C=CC=CC=3)NC=2)=O)=C1 HOWAWNVFEFCJAO-UHFFFAOYSA-N 0.000 description 1
HNXCXJWVOJMDPN-UHFFFAOYSA-N CCOC(C)=O.I Chemical compound CCOC(C)=O.I HNXCXJWVOJMDPN-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
229940007550 benzyl acetate Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyloxyacetoaldehyde Natural products CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
SHTBTGXNVWYODU-UHFFFAOYSA-N hydron;(3-methylphenyl)hydrazine;chloride Chemical compound Cl.CC1=CC=CC(NN)=C1 SHTBTGXNVWYODU-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
OXYLCGRXCQARQV-UHFFFAOYSA-N methyl 2-(3-fluorophenyl)acetate Chemical compound COC(=O)CC1=CC=CC(F)=C1 OXYLCGRXCQARQV-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU762427094A 1975-12-11 1976-12-10 Способ получени производных 1,4-дифенил-3-пиразолин-5-она SU643083A3 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US63974475A	1975-12-11	1975-12-11
US05/724,502 US4075003A (en)	1975-12-11	1976-09-20	Novel herbicidal method utilizing 1,4-diphenyl-3-pyrazolin-5-ones

Publications (1)

Publication Number	Publication Date
SU643083A3 true SU643083A3 (ru)	1979-01-15

Family

ID=27093389

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU762427094A SU643083A3 (ru)	1975-12-11	1976-12-10	Способ получени производных 1,4-дифенил-3-пиразолин-5-она

Country Status (28)

Country	Link
JP (1)	JPS6033112B2 (cs)
AR (1)	AR218861A1 (cs)
AT (1)	AT354434B (cs)
AU (1)	AU507882B2 (cs)
BG (1)	BG27547A3 (cs)
CA (1)	CA1067907A (cs)
CH (1)	CH622784A5 (cs)
CS (1)	CS186746B2 (cs)
DD (1)	DD129326A5 (cs)
DE (1)	DE2651008A1 (cs)
DK (1)	DK550876A (cs)
ES (1)	ES454061A1 (cs)
FR (1)	FR2334674A1 (cs)
GB (1)	GB1570623A (cs)
GR (1)	GR63123B (cs)
IE (1)	IE43807B1 (cs)
IL (1)	IL50792A (cs)
IT (1)	IT1123686B (cs)
MX (1)	MX3832E (cs)
NL (1)	NL7613810A (cs)
NZ (1)	NZ182530A (cs)
PH (1)	PH13076A (cs)
PL (1)	PL106071B1 (cs)
PT (1)	PT65890B (cs)
RO (1)	RO72400B (cs)
SE (1)	SE430413B (cs)
SU (1)	SU643083A3 (cs)
ZA (1)	ZA766561B (cs)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK529378A (da) *	1978-01-09	1979-07-10	Shell Int Research	Anilidderivater
NZ213630A (en) *	1984-10-19	1990-02-26	Ici Plc	Acrylic acid derivatives and fungicidal compositions
DE3527157A1 (de)	1985-07-30	1987-02-12	Bayer Ag	1-heteroaryl-4-aryl-pyrazol-derivate
DE102008020113A1 (de)	2008-04-23	2009-10-29	Bayer Schering Pharma Aktiengesellschaft	Substituierte Dihydropyrazolone und ihre Verwendung
DE102005019712A1 (de)	2005-04-28	2006-11-09	Bayer Healthcare Ag	Dipyridyl-dihydropyrazolone und ihre Verwendung
DE102006050513A1 (de)	2006-10-26	2008-04-30	Bayer Healthcare Ag	Substitiuierte Dihydropyrazolone und ihre Verwendung
DE102006050515A1 (de)	2006-10-26	2008-04-30	Bayer Healthcare Ag	Substituierte Dipyridiyl-dihydropyrazolone und ihre Verwendung
DE102006050516A1 (de)	2006-10-26	2008-04-30	Bayer Healthcare Ag	Substituierte Dihydropyrazolone und ihre Verwendung
DE102007044032A1 (de)	2007-09-14	2009-03-19	Bayer Healthcare Ag	Substituierte heterocyclische Verbindungen und ihre Verwendung
DE102007048447A1 (de)	2007-10-10	2009-04-16	Bayer Healthcare Ag	Substituierte Dihydropyrazolthione und ihre Verwendung
DE102010044131A1 (de)	2010-11-18	2012-05-24	Bayer Schering Pharma Aktiengesellschaft	Substituiertes Natrium-1H-pyrazol-5-olat

1976
- 1976-10-25 GR GR52014A patent/GR63123B/el unknown
- 1976-10-28 IL IL50792A patent/IL50792A/xx unknown
- 1976-10-29 CA CA264,490A patent/CA1067907A/en not_active Expired
- 1976-11-01 IE IE2429/76A patent/IE43807B1/en unknown
- 1976-11-02 ZA ZA00766561A patent/ZA766561B/xx unknown
- 1976-11-04 NZ NZ182530A patent/NZ182530A/xx unknown
- 1976-11-05 PH PH19097A patent/PH13076A/en unknown
- 1976-11-08 DE DE19762651008 patent/DE2651008A1/de not_active Withdrawn
- 1976-11-25 SE SE7613239A patent/SE430413B/xx unknown
- 1976-11-25 PT PT65890A patent/PT65890B/pt unknown
- 1976-11-26 AR AR265630A patent/AR218861A1/es active
- 1976-12-02 ES ES454061A patent/ES454061A1/es not_active Expired
- 1976-12-02 CH CH1520676A patent/CH622784A5/de not_active IP Right Cessation
- 1976-12-04 RO RO88642A patent/RO72400B/ro unknown
- 1976-12-06 GB GB50713/76A patent/GB1570623A/en not_active Expired
- 1976-12-06 MX MX765189U patent/MX3832E/es unknown
- 1976-12-06 FR FR7636699A patent/FR2334674A1/fr active Granted
- 1976-12-07 CS CS7600007973A patent/CS186746B2/cs unknown
- 1976-12-08 DK DK550876A patent/DK550876A/da not_active Application Discontinuation
- 1976-12-08 DD DD7600196193A patent/DD129326A5/xx unknown
- 1976-12-09 BG BG034872A patent/BG27547A3/xx unknown
- 1976-12-09 AT AT911876A patent/AT354434B/de not_active IP Right Cessation
- 1976-12-09 AU AU20436/76A patent/AU507882B2/en not_active Expired
- 1976-12-10 PL PL1976194292A patent/PL106071B1/pl unknown
- 1976-12-10 SU SU762427094A patent/SU643083A3/ru active
- 1976-12-10 IT IT30299/76A patent/IT1123686B/it active
- 1976-12-11 JP JP51149321A patent/JPS6033112B2/ja not_active Expired
- 1976-12-13 NL NL7613810A patent/NL7613810A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
GB1570623A (en)	1980-07-02
DD129326A5 (de)	1978-01-11
PT65890B (en)	1978-05-18
CH622784A5 (en)	1981-04-30
CS186746B2 (en)	1978-12-29
AR218861A1 (es)	1980-07-15
PH13076A (en)	1979-11-23
SE430413B (sv)	1983-11-14
GR63123B (en)	1979-09-11
IT1123686B (it)	1986-04-30
RO72400B (ro)	1983-04-30
ATA911876A (de)	1979-06-15
MX3832E (es)	1981-08-04
JPS5273868A (en)	1977-06-21
IE43807L (en)	1977-06-11
FR2334674B1 (cs)	1980-11-07
NZ182530A (en)	1978-06-20
SE7613239L (sv)	1977-06-12
BG27547A3 (en)	1979-11-12
FR2334674A1 (fr)	1977-07-08
AU2043676A (en)	1978-06-15
CA1067907A (en)	1979-12-11
DE2651008A1 (de)	1977-06-23
DK550876A (da)	1977-06-12
ES454061A1 (es)	1978-03-01
NL7613810A (nl)	1977-06-14
AU507882B2 (en)	1980-02-28
PT65890A (en)	1976-12-01
IE43807B1 (en)	1981-06-03
ZA766561B (en)	1978-06-28
IL50792A0 (en)	1976-12-31
IL50792A (en)	1979-05-31
RO72400A (ro)	1983-04-29
JPS6033112B2 (ja)	1985-08-01
AT354434B (de)	1979-01-10
PL106071B1 (pl)	1979-11-30

Publication	Publication Date	Title
US4841047A (en)	1989-06-20	4-benzyl-1-(2H)-phthalazinone-derivates
SU643083A3 (ru)	1979-01-15	Способ получени производных 1,4-дифенил-3-пиразолин-5-она
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