CA1067906A - Series of 1-arylmethyl-2-imidazolidinones - Google Patents
Series of 1-arylmethyl-2-imidazolidinonesInfo
- Publication number
- CA1067906A CA1067906A CA245,212A CA245212A CA1067906A CA 1067906 A CA1067906 A CA 1067906A CA 245212 A CA245212 A CA 245212A CA 1067906 A CA1067906 A CA 1067906A
- Authority
- CA
- Canada
- Prior art keywords
- imidazolidinone
- reacted
- chemical equivalent
- obvious chemical
- bromo
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- -1 5-bromo-2-naphthyl Chemical group 0.000 claims description 4
- IONDHVFVKHWVCR-UHFFFAOYSA-N 1-benzhydrylimidazolidin-2-one Chemical compound O=C1NCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 IONDHVFVKHWVCR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
- LBOBESSDSGODDD-UHFFFAOYSA-N 1,3-dichloro-2-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C=CC=C1Cl LBOBESSDSGODDD-UHFFFAOYSA-N 0.000 claims description 2
- MOBRMRJUKNQBMY-UHFFFAOYSA-N 1-(chloromethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CCl MOBRMRJUKNQBMY-UHFFFAOYSA-N 0.000 claims description 2
- YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 claims description 2
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims description 2
- VTGRVYJPIVZZGS-UHFFFAOYSA-N 4-(chloromethyl)-1,2-difluorobenzene Chemical compound FC1=CC=C(CCl)C=C1F VTGRVYJPIVZZGS-UHFFFAOYSA-N 0.000 claims description 2
- KMWZXXDWPVRYMA-UHFFFAOYSA-N 1-(naphthalen-2-ylmethyl)imidazolidin-2-one Chemical compound O=C1NCCN1CC1=CC=C(C=CC=C2)C2=C1 KMWZXXDWPVRYMA-UHFFFAOYSA-N 0.000 claims 2
- ZDOKUMSQIKUWOS-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]imidazolidin-2-one Chemical compound ClC1=CC=CC(Cl)=C1CN1C(=O)NCC1 ZDOKUMSQIKUWOS-UHFFFAOYSA-N 0.000 claims 2
- HSFHHBMXLUGNAF-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]imidazolidin-2-one Chemical compound FC1=CC=CC=C1CN1C(=O)NCC1 HSFHHBMXLUGNAF-UHFFFAOYSA-N 0.000 claims 2
- DMYNEPYMKWEFAC-UHFFFAOYSA-N 1-[(2-hydroxy-5-nitrophenyl)methyl]imidazolidin-2-one Chemical compound OC1=CC=C([N+]([O-])=O)C=C1CN1C(=O)NCC1 DMYNEPYMKWEFAC-UHFFFAOYSA-N 0.000 claims 2
- AZRLPEYKPQHLAY-UHFFFAOYSA-N 1-[(3,4-difluorophenyl)methyl]imidazolidin-2-one Chemical compound C1=C(F)C(F)=CC=C1CN1C(=O)NCC1 AZRLPEYKPQHLAY-UHFFFAOYSA-N 0.000 claims 2
- WRXZUWLGKCULFV-UHFFFAOYSA-N 1-[(4-bromophenyl)methyl]imidazolidin-2-one Chemical compound C1=CC(Br)=CC=C1CN1C(=O)NCC1 WRXZUWLGKCULFV-UHFFFAOYSA-N 0.000 claims 2
- XONYERRJRPQJLX-UHFFFAOYSA-N 1-[(4-phenylmethoxyphenyl)methyl]imidazolidin-2-one Chemical compound O=C1NCCN1CC(C=C1)=CC=C1OCC1=CC=CC=C1 XONYERRJRPQJLX-UHFFFAOYSA-N 0.000 claims 2
- DQZRYKOIKLEBBD-UHFFFAOYSA-N 1-[(5-bromonaphthalen-2-yl)methyl]imidazolidin-2-one Chemical compound C=1C=C2C(Br)=CC=CC2=CC=1CN1CCNC1=O DQZRYKOIKLEBBD-UHFFFAOYSA-N 0.000 claims 2
- YJQPAAFBOXDXCD-UHFFFAOYSA-N 4-[(2-oxoimidazolidin-1-yl)methyl]benzonitrile Chemical compound O=C1NCCN1CC1=CC=C(C#N)C=C1 YJQPAAFBOXDXCD-UHFFFAOYSA-N 0.000 claims 2
- UYQPSKUPEXAQRJ-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylmethoxybenzene Chemical compound C1=CC(CCl)=CC=C1OCC1=CC=CC=C1 UYQPSKUPEXAQRJ-UHFFFAOYSA-N 0.000 claims 1
- SXEJKULVPDPHDU-UHFFFAOYSA-N 1-[(2,4-dichlorophenyl)methyl]imidazolidin-2-one Chemical compound ClC1=CC(Cl)=CC=C1CN1C(=O)NCC1 SXEJKULVPDPHDU-UHFFFAOYSA-N 0.000 claims 1
- IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 claims 1
- KFDPCYZHENQOBV-UHFFFAOYSA-N 2-(bromomethyl)-4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1CBr KFDPCYZHENQOBV-UHFFFAOYSA-N 0.000 claims 1
- MPCHQYWZAVTABQ-UHFFFAOYSA-N 2-(chloromethyl)naphthalene Chemical compound C1=CC=CC2=CC(CCl)=CC=C21 MPCHQYWZAVTABQ-UHFFFAOYSA-N 0.000 claims 1
- UMLFTCYAQPPZER-UHFFFAOYSA-N 4-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=C(C#N)C=C1 UMLFTCYAQPPZER-UHFFFAOYSA-N 0.000 claims 1
- FXBSPTMCLZCDSP-UHFFFAOYSA-N 6-bromo-1-(chloromethyl)naphthalene Chemical compound BrC1=CC=C2C(CCl)=CC=CC2=C1 FXBSPTMCLZCDSP-UHFFFAOYSA-N 0.000 claims 1
- ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 239000012043 crude product Substances 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000000538 analytical sample Substances 0.000 description 6
- 239000002026 chloroform extract Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KPOFUVXADIRQLG-UHFFFAOYSA-N (6-bromonaphthalen-1-yl)methanol Chemical compound BrC1=CC=C2C(CO)=CC=CC2=C1 KPOFUVXADIRQLG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- QPOQPJDDJJNVRY-UHFFFAOYSA-N 5-bromonaphthalene-2-carboxylic acid Chemical compound BrC1=CC=CC2=CC(C(=O)O)=CC=C21 QPOQPJDDJJNVRY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-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
- 241000357437 Mola Species 0.000 description 1
- 241001077660 Molo Species 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/18—Preparation of halogenated hydrocarbons by replacement by halogens of oxygen atoms of carbonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/72—Polycyclic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/547,925 US3932452A (en) | 1975-02-07 | 1975-02-07 | 1-Arylmethyl-2-imidazolidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067906A true CA1067906A (en) | 1979-12-11 |
Family
ID=24186700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA245,212A Expired CA1067906A (en) | 1975-02-07 | 1976-02-06 | Series of 1-arylmethyl-2-imidazolidinones |
Country Status (10)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4063022A (en) * | 1976-11-22 | 1977-12-13 | Morton-Norwich Products, Inc. | Antisecretory 2-imidazolidinones |
| US4287344A (en) * | 1977-08-03 | 1981-09-01 | Abidzhan Safaev | N,N-bis-(decahydroquinolyl-N-methyl)imidazolin-2-thiones |
| US4677131A (en) * | 1985-11-01 | 1987-06-30 | Merck & Co., Inc. | Cyclic ureas as dermal penetration enhancers |
| US5270317A (en) * | 1990-03-20 | 1993-12-14 | Elf Sanofi | N-substituted heterocyclic derivatives, their preparation and the pharmaceutical compositions in which they are present |
| DE19532668A1 (de) * | 1995-09-05 | 1997-03-06 | Dresden Arzneimittel | Neue, antikonvulsiv wirkende 1-Ar(alk)yl-imidazolin-2-one, die in 4-Stellung einen disubstituierten Amin-Rest enthalten, und Verfahren zu deren Herstellung |
| US20050070537A1 (en) | 2002-10-10 | 2005-03-31 | Chris Rundfeldt | Use of dihydroimidazolones for the treatment of dogs |
| US9820988B2 (en) | 2014-03-24 | 2017-11-21 | Boehringer Ingelheim Vetmedica Gmbh | Treatment of epileptic disorders in feline animals |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3196152A (en) * | 1965-07-20 | Phenyl and alkyleneamino substituted imidazolidinones and salts thereof | ||
| US2518264A (en) * | 1946-01-23 | 1950-08-08 | American Cyanamid Co | Method of preparing imidazolidones |
| US2514380A (en) * | 1946-12-26 | 1950-07-11 | Hoffmann La Roche | Diamines and method of production |
| US3459757A (en) * | 1965-10-22 | 1969-08-05 | American Cyanamid Co | Imidazolidines |
| US3636039A (en) * | 1970-02-24 | 1972-01-18 | Hoffmann La Roche | Substituted benzylimidazolidinones |
-
1975
- 1975-02-07 US US05/547,925 patent/US3932452A/en not_active Expired - Lifetime
- 1975-10-27 GB GB4412175A patent/GB1468334A/en not_active Expired
- 1975-11-05 NL NL7512968A patent/NL7512968A/xx not_active Application Discontinuation
- 1975-12-05 SE SE7513711A patent/SE7513711L/xx unknown
- 1975-12-10 ES ES443371A patent/ES443371A1/es not_active Expired
-
1976
- 1976-01-30 JP JP51008578A patent/JPS51100075A/ja active Pending
- 1976-02-04 BE BE164101A patent/BE838278A/xx unknown
- 1976-02-06 CA CA245,212A patent/CA1067906A/en not_active Expired
- 1976-02-06 FR FR7603350A patent/FR2299865A1/fr active Granted
- 1976-02-06 DE DE19762604727 patent/DE2604727A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US3932452A (en) | 1976-01-13 |
| SE7513711L (sv) | 1976-08-09 |
| ES443371A1 (es) | 1977-05-01 |
| BE838278A (fr) | 1976-08-04 |
| JPS51100075A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-03 |
| DE2604727A1 (de) | 1976-08-19 |
| GB1468334A (en) | 1977-03-23 |
| AU8599975A (en) | 1977-04-28 |
| NL7512968A (nl) | 1976-08-10 |
| FR2299865B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-06-27 |
| FR2299865A1 (fr) | 1976-09-03 |
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