NO781618L - Fremgangsmaate ved fremstilling av nye chromenderivater - Google Patents

Fremgangsmaate ved fremstilling av nye chromenderivater

Info

Publication number: NO781618L
Authority: NO; Norway
Prior art keywords: radical; formula; carbon atoms; denotes; alkyl
Prior art date: 1977-05-09

Application number

NO781618A

Other languages

English (en)

Norwegian (no)

Inventor

Serge Beranger

Henri Pinhas

Original Assignee

Laroche Navarron Sa

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.)

1977-05-09

Filing date

1978-05-08

Publication date

1978-11-10

1978-05-08 Application filed by Laroche Navarron Sa filed Critical Laroche Navarron Sa

1978-11-10 Publication of NO781618L publication Critical patent/NO781618L/no

Links

238000000034 method Methods 0.000 title claims description 8
150000008371 chromenes Chemical class 0.000 title description 2
-1 alkoxy radical Chemical class 0.000 claims description 51
125000004432 carbon atom Chemical group C* 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 33
150000003254 radicals Chemical class 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
150000001298 alcohols Chemical class 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000000463 material Substances 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000243 solution Substances 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
208000009079 Bronchial Spasm Diseases 0.000 description 3
208000014181 Bronchial disease Diseases 0.000 description 3
206010006482 Bronchospasm Diseases 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
SPWAIRGUACCVAD-UHFFFAOYSA-N 1-(2h-chromen-3-yl)ethanone Chemical compound C1=CC=C2OCC(C(=O)C)=CC2=C1 SPWAIRGUACCVAD-UHFFFAOYSA-N 0.000 description 2
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
230000006793 arrhythmia Effects 0.000 description 2
230000003182 bronchodilatating effect Effects 0.000 description 2
229940124630 bronchodilator Drugs 0.000 description 2
239000013078 crystal Substances 0.000 description 2
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
230000033764 rhythmic process Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 description 1
DPSJKWCTFLQCJC-UHFFFAOYSA-N 1-(2H-chromen-2-yl)ethanone Chemical compound C1=CC=C2C=CC(C(=O)C)OC2=C1 DPSJKWCTFLQCJC-UHFFFAOYSA-N 0.000 description 1
CJNVMWOFHMIXBS-UHFFFAOYSA-N 1-(2h-chromen-3-yl)-2-(4-phenylpiperazin-1-yl)ethanol;hydrochloride Chemical compound Cl.C=1C2=CC=CC=C2OCC=1C(O)CN(CC1)CCN1C1=CC=CC=C1 CJNVMWOFHMIXBS-UHFFFAOYSA-N 0.000 description 1
RTXOQMZAZKURNH-UHFFFAOYSA-N 1-(2h-chromen-3-yl)-2-(4-phenylpiperazin-1-yl)ethanone;hydrochloride Chemical compound Cl.C=1C2=CC=CC=C2OCC=1C(=O)CN(CC1)CCN1C1=CC=CC=C1 RTXOQMZAZKURNH-UHFFFAOYSA-N 0.000 description 1
WDXVIENSHOAFRM-UHFFFAOYSA-N 1-(2h-chromen-3-yl)-3-(4-methylpiperazin-1-yl)propan-1-ol;hydrochloride Chemical compound Cl.C1CN(C)CCN1CCC(O)C1=CC2=CC=CC=C2OC1 WDXVIENSHOAFRM-UHFFFAOYSA-N 0.000 description 1
QUMRLXXCRQWODL-UHFFFAOYSA-N 1-methylpiperazin-1-ium;chloride Chemical compound [Cl-].C[NH+]1CCNCC1 QUMRLXXCRQWODL-UHFFFAOYSA-N 0.000 description 1
DSUVJRDETHXEBP-UHFFFAOYSA-N 2-bromo-1-(2h-chromen-3-yl)ethanone Chemical compound C1=CC=C2OCC(C(=O)CBr)=CC2=C1 DSUVJRDETHXEBP-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
241000700198 Cavia Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
238000006683 Mannich reaction Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241001122767 Theaceae Species 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
239000003416 antiarrhythmic agent Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
150000001844 chromium Chemical class 0.000 description 1
230000007665 chronic toxicity Effects 0.000 description 1
231100000160 chronic toxicity Toxicity 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid 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
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
229960003343 ouabain Drugs 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
206010047302 ventricular tachycardia Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)

NO781618A 1977-05-09 1978-05-08 Fremgangsmaate ved fremstilling av nye chromenderivater NO781618L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB19351/77A GB1583811A (en)	1977-05-09	1977-05-09	Chromene derivatives

Publications (1)

Publication Number	Publication Date
NO781618L true NO781618L (no)	1978-11-10

Family

ID=10127911

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO781618A NO781618L (no)	1977-05-09	1978-05-08	Fremgangsmaate ved fremstilling av nye chromenderivater

Country Status (21)

Country	Link
US (1)	US4181722A (da)
JP (1)	JPS53149978A (da)
AR (1)	AR219746A1 (da)
AT (1)	AT361921B (da)
AU (1)	AU519864B2 (da)
BE (1)	BE866784A (da)
CA (1)	CA1099717A (da)
CH (1)	CH632261A5 (da)
DE (1)	DE2819896A1 (da)
DK (1)	DK199778A (da)
ES (1)	ES469961A1 (da)
FR (1)	FR2390445A1 (da)
GB (1)	GB1583811A (da)
IE (1)	IE46823B1 (da)
IL (1)	IL54576A (da)
IT (1)	IT7868045A0 (da)
NL (1)	NL7804907A (da)
NO (1)	NO781618L (da)
NZ (1)	NZ187202A (da)
PH (1)	PH13728A (da)
ZA (1)	ZA782622B (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4288447A (en) *	1979-02-06	1981-09-08	A. H. Robins Company, Inc.	Antihyperglycemic 4-substituted 2-iminoimidazolidine compositions
US4288591A (en) *	1979-02-06	1981-09-08	A. H. Robins Company, Inc.	4-Substituted 2-iminoimidazolidine compounds
US4329459A (en) *	1980-05-05	1982-05-11	The Upjohn Company	Tetrahydrobenzopyran derivatives
US4971982A (en) *	1987-07-06	1990-11-20	Hoffmann-La Roche Inc.	Benzopyran derivatives
FR2618437B1 (fr) *	1987-07-23	1989-11-17	Rhone Poulenc Sante	Nouveaux derives du benzopyranne, leur preparation et les medicaments qui les contiennent
US6693099B2 (en)	2000-10-17	2004-02-17	The Procter & Gamble Company	Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance
US6376514B1 (en) *	2000-10-17	2002-04-23	The Procter & Gamble Co.	Substituted six-membered heterocyclic compounds useful for treating multidrug resistance and compositions and methods thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3374245A (en) *	1964-04-01	1968-03-19	Ciba Geigy Corp	Unsaturated oxacycles
US3959281A (en) *	1968-01-19	1976-05-25	Cassella Farbwerke Mainkur Aktiengesellschaft	Piperazino substituted coumarin derivatives
US3796727A (en) *	1972-01-31	1974-03-12	Eastman Kodak Co	Synthesis of novel benzopyran compounds
DE2325633A1 (de) *	1973-05-21	1974-12-12	Boehringer Sohn Ingelheim	Piperazinderivate

1977
- 1977-05-09 GB GB19351/77A patent/GB1583811A/en not_active Expired
1978
- 1978-04-05 AR AR272065A patent/AR219746A1/es active
- 1978-04-25 CH CH443078A patent/CH632261A5/fr not_active IP Right Cessation
- 1978-04-25 IL IL54576A patent/IL54576A/xx unknown
- 1978-05-01 US US05/901,834 patent/US4181722A/en not_active Expired - Lifetime
- 1978-05-03 FR FR7813114A patent/FR2390445A1/fr active Granted
- 1978-05-06 DE DE19782819896 patent/DE2819896A1/de not_active Withdrawn
- 1978-05-08 CA CA302,786A patent/CA1099717A/en not_active Expired
- 1978-05-08 BE BE187457A patent/BE866784A/xx unknown
- 1978-05-08 NL NL7804907A patent/NL7804907A/xx not_active Application Discontinuation
- 1978-05-08 ZA ZA00782622A patent/ZA782622B/xx unknown
- 1978-05-08 DK DK199778A patent/DK199778A/da not_active Application Discontinuation
- 1978-05-08 JP JP5382678A patent/JPS53149978A/ja active Pending
- 1978-05-08 IT IT7868045A patent/IT7868045A0/it unknown
- 1978-05-08 NZ NZ187202A patent/NZ187202A/xx unknown
- 1978-05-08 AU AU35899/78A patent/AU519864B2/en not_active Expired
- 1978-05-08 IE IE926/78A patent/IE46823B1/en unknown
- 1978-05-08 NO NO781618A patent/NO781618L/no unknown
- 1978-05-09 ES ES469961A patent/ES469961A1/es not_active Expired
- 1978-05-09 AT AT336278A patent/AT361921B/de not_active IP Right Cessation
1980
- 1980-05-09 PH PH21117A patent/PH13728A/en unknown

Also Published As

Publication number	Publication date
IT7868045A0 (it)	1978-05-08
IE46823B1 (en)	1983-10-05
FR2390445A1 (fr)	1978-12-08
FR2390445B1 (da)	1982-03-12
ZA782622B (en)	1979-05-30
AR219746A1 (es)	1980-09-15
ATA336278A (de)	1980-09-15
NL7804907A (nl)	1978-11-13
CH632261A5 (fr)	1982-09-30
ES469961A1 (es)	1978-12-16
IL54576A0 (en)	1978-07-31
IL54576A (en)	1981-07-31
AT361921B (de)	1981-04-10
AU3589978A (en)	1979-11-15
DK199778A (da)	1978-11-10
IE780926L (en)	1978-11-09
DE2819896A1 (de)	1978-11-23
US4181722A (en)	1980-01-01
PH13728A (en)	1980-09-09
AU519864B2 (en)	1981-12-24
CA1099717A (en)	1981-04-21
NZ187202A (en)	1979-10-25
GB1583811A (en)	1981-02-04
BE866784A (fr)	1978-11-08
JPS53149978A (en)	1978-12-27

Publication	Publication Date	Title
US5346896A (en)	1994-09-13	1-(aryl or heteroaryl)-4[ω-(aryl or heteroaryl)ω-(aryl or heteroaryl)alkylene]piperazines
CA1193264A (en)	1985-09-10	Pharmaceutically active (3-aminopropoxy)bibenzyl derivatives
US2683742A (en)	1954-07-13	Nu, nu-disubstituted omega-arylmethoxy-omega-arylalkylamine derivatives
US4478750A (en)	1984-10-23	1-Phenyl-azepinoindoles
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