DE2017265A1 - l-(omega-substituierte-Alkyl)-2mehtylbenzimidazole und Verfahren zu deren Herstellung - Google Patents
l-(omega-substituierte-Alkyl)-2mehtylbenzimidazole und Verfahren zu deren HerstellungInfo
- Publication number
- DE2017265A1 DE2017265A1 DE19702017265 DE2017265A DE2017265A1 DE 2017265 A1 DE2017265 A1 DE 2017265A1 DE 19702017265 DE19702017265 DE 19702017265 DE 2017265 A DE2017265 A DE 2017265A DE 2017265 A1 DE2017265 A1 DE 2017265A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- methylbenzimidazole
- ethyl
- sub
- phenylpiperazinyl
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 12
- -1 4-phenylpiperazinyl Chemical group 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000004480 active ingredient Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
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- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- NBFQYHKHPBMJJV-UHFFFAOYSA-N risocaine Chemical compound CCCOC(=O)C1=CC=C(N)C=C1 NBFQYHKHPBMJJV-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009284 tracheal contraction Effects 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81444269A | 1969-04-08 | 1969-04-08 | |
| US81444369A | 1969-04-08 | 1969-04-08 | |
| US81549569A | 1969-04-11 | 1969-04-11 | |
| US81549269A | 1969-04-11 | 1969-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2017265A1 true DE2017265A1 (de) | 1970-10-15 |
Family
ID=27505843
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702017265 Pending DE2017265A1 (de) | 1969-04-08 | 1970-04-10 | l-(omega-substituierte-Alkyl)-2mehtylbenzimidazole und Verfahren zu deren Herstellung |
| DE19702017255 Pending DE2017255A1 (de) | 1969-04-08 | 1970-04-10 | 1-substituierte-3-Pheny!pyrrolidine und Verfahren zu deren Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702017255 Pending DE2017255A1 (de) | 1969-04-08 | 1970-04-10 | 1-substituierte-3-Pheny!pyrrolidine und Verfahren zu deren Herstellung |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US3647790A (en16) |
| AT (1) | AT294815B (en16) |
| BE (1) | BE748392A (en16) |
| CA (1) | CA974995A (en16) |
| CH (2) | CH556336A (en16) |
| DE (2) | DE2017265A1 (en16) |
| FR (2) | FR2042321B1 (en16) |
| GB (2) | GB1299621A (en16) |
| NL (1) | NL7005191A (en16) |
| SE (1) | SE366040B (en16) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2723091A1 (fr) * | 1994-07-29 | 1996-02-02 | Esteve Labor Dr | Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles |
| WO1996004250A1 (en) * | 1994-08-05 | 1996-02-15 | Pfizer Inc. | Benzimidazole derivatives having dopaminergic activity |
| US5883094A (en) * | 1995-04-24 | 1999-03-16 | Pfizer Inc. | Benzimidazolone derivatives with central dopaminergic activity |
| US5889010A (en) * | 1995-05-18 | 1999-03-30 | Pfizer Inc. | Benzimidazole derivatives having dopaminergic activity |
| US6355659B1 (en) | 1994-07-29 | 2002-03-12 | Laboratorios Del Dr. Esteve, S.A. | 4-(4-Chlorophenyl)-1236-tetrahydro-1(1H-124-triazol-1-yl)butty)pyrideine and salts thereof; pharmaceutical compositions and method of treating psychoses utilizing same |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2541855A1 (de) * | 1975-09-18 | 1977-03-31 | Schering Ag | 4-(polyalkoxy-phenyl)-2-pyrrolidone ii |
| US4066772A (en) * | 1975-07-21 | 1978-01-03 | Janssen Pharmaceutica N.V. | 1,3-Dihydro-1-[3-(1-piperidinyl)propyl]-2H-benzimidazol-2-ones and related compounds |
| US4175129A (en) | 1975-07-21 | 1979-11-20 | Janssen Pharmaceutica N.V. | Antiemetic 1-(benzoxazolylalkyl)-piperidine derivatives |
| US4035369A (en) * | 1975-10-08 | 1977-07-12 | Janssen Pharmaceutica N.V. | 1-Benzazolylalkyl-4-substituted-piperidines |
| US4126688A (en) * | 1976-05-17 | 1978-11-21 | Janssen Pharmaceutica N.V. | Antiemetic 1-(benzotriazolyl-alkyl)-piperidine derivatives |
| LU75478A1 (en16) * | 1976-07-28 | 1978-02-08 | ||
| US4241061A (en) * | 1979-05-21 | 1980-12-23 | International Minerals & Chemical Corp. | Oxazolidinyl-quinoxalines and use as growth promoters |
| US4303667A (en) * | 1979-05-25 | 1981-12-01 | Nippon Soda Company Limited | Phenylprrole derivatives |
| AU542153B2 (en) * | 1979-12-05 | 1985-02-07 | Per Arvid Emil Carlsson | New phenyl-azacycloalkanes |
| US4656276A (en) * | 1980-08-07 | 1987-04-07 | Angus Chemical Company | Quinoxaline adducts useful as anthelmintics |
| US4720548A (en) * | 1980-08-07 | 1988-01-19 | Angus Chemical Company | Quinoxaline adducts useful as anthelmintics |
| US4629790A (en) * | 1980-08-07 | 1986-12-16 | Angus Chemical Company | Quinoxaline adducts useful as anthelmintics |
| US4658028A (en) * | 1980-08-07 | 1987-04-14 | Angus Chemical Company | Quinoxaline adducts useful as anthelmintics |
| US4661593A (en) * | 1980-08-07 | 1987-04-28 | Angus Chemcial Company | Quinoxaline adducts useful as anthelmintics |
| US4348389A (en) * | 1980-08-07 | 1982-09-07 | International Minerals & Chemical Corp. | Quinoxaline adducts useful as anthelmintics |
| DE3328643A1 (de) * | 1983-08-09 | 1985-02-21 | Gödecke AG, 1000 Berlin | 3-aryl-3-pyrrolin-derivate, verfahren zu deren herstellung sowie deren verwendung bei der bekaempfung von herz- und gefaesskrankheiten |
| US5118816A (en) * | 1990-12-26 | 1992-06-02 | American Cyanamid Company | 2-aryl-5-(trifluoromethyl)-2-pyrroline compounds useful in the manufacture of insecticidal, nematocidal and acaricidal arylpyrroles |
| US5514678A (en) * | 1992-03-26 | 1996-05-07 | E. I. Du Pont De Nemours And Company | Arthropodicidal 1,2,4-triazinyl amides |
| US5665754A (en) * | 1993-09-20 | 1997-09-09 | Glaxo Wellcome Inc. | Substituted pyrrolidines |
| DE19615232A1 (de) * | 1996-04-18 | 1997-10-23 | Merck Patent Gmbh | Neue Carbamoylderivate und deren Verwendung als 5-HT ¶1¶¶A¶-Antagonisten |
| GB9801392D0 (en) * | 1998-01-22 | 1998-03-18 | Smithkline Beecham Plc | Novel compounds |
| IL165624A0 (en) * | 2002-06-14 | 2006-01-15 | Merck & Co Inc | Mitotic kinesin inhibitors |
| US7301028B2 (en) * | 2002-06-14 | 2007-11-27 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| EP1556052A4 (en) * | 2002-10-18 | 2006-11-02 | Merck & Co Inc | MITOTIC KINESINE HEMMER |
| EP1656133A4 (en) * | 2003-08-15 | 2008-10-29 | Merck & Co Inc | INHIBITORS OF MITOTIC KINESINE |
| SI1664026T1 (sl) * | 2003-08-15 | 2009-04-30 | Merck & Co Inc | Inhibitorji mitotiäśnega kinezina |
| JP2007502773A (ja) * | 2003-08-15 | 2007-02-15 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害薬 |
| US7829589B2 (en) * | 2005-06-10 | 2010-11-09 | Elixir Pharmaceuticals, Inc. | Sulfonamide compounds and uses thereof |
| WO2006135860A1 (en) * | 2005-06-10 | 2006-12-21 | Elixir Pharmaceuticals, Inc. | Sulfonamide compounds and uses thereof |
| FR2902790A1 (fr) * | 2006-06-27 | 2007-12-28 | Sanofi Aventis Sa | Derives d'urees de piperidine ou pyrrolidine,leur preparation et leur application en therapeutique |
| CN101808987A (zh) * | 2007-06-05 | 2010-08-18 | Nsab神经研究瑞典公司分公司 | 作为皮层儿茶酚胺能神经传递调节剂的二取代的苯基吡咯烷 |
| CN101711234A (zh) * | 2007-06-05 | 2010-05-19 | Nsab神经研究瑞典公司分公司 | 作为皮层儿茶酚胺能神经传递调节剂的新型二取代的苯基吡咯烷 |
| TWI457122B (zh) * | 2007-07-20 | 2014-10-21 | Orion Corp | 作為用於治療周邊和中央神經系統疾病之alpha2C拮抗劑的2,3－二氫苯並[1,4]戴奧辛－2－基甲基衍生物 |
| MX2011005036A (es) | 2008-11-24 | 2011-06-16 | Nsab Af Neurosearch Sweden Ab | Derivados de 3-fenil-3metoxipirrolidina como moduladores de la neurotransmision catecolaminergia cortical. |
| JOP20190050A1 (ar) | 2016-09-23 | 2019-03-20 | Bial Portela & C? S A | مثبطات دوبامين-b-هيدروكسيلاز تخترق حاجز المخ الدموي |
| SG11202004231YA (en) | 2017-12-04 | 2020-06-29 | BIAL PORTELA & Cª S A | Dopamine-β-hydroxylase inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3362956A (en) * | 1965-08-19 | 1968-01-09 | Sterling Drug Inc | 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines |
-
1969
- 1969-04-08 US US814442A patent/US3647790A/en not_active Expired - Lifetime
- 1969-04-08 US US814443A patent/US3635982A/en not_active Expired - Lifetime
- 1969-04-11 US US815495A patent/US3644414A/en not_active Expired - Lifetime
- 1969-04-11 US US815492A patent/US3634441A/en not_active Expired - Lifetime
-
1970
- 1970-02-20 CH CH250270A patent/CH556336A/xx not_active IP Right Cessation
- 1970-02-20 CH CH249470A patent/CH549038A/xx not_active IP Right Cessation
- 1970-03-24 GB GB04118/70A patent/GB1299621A/en not_active Expired
- 1970-04-02 BE BE748392D patent/BE748392A/xx unknown
- 1970-04-07 GB GB1289089D patent/GB1289089A/en not_active Expired
- 1970-04-09 SE SE04844/70A patent/SE366040B/xx unknown
- 1970-04-09 AT AT325570A patent/AT294815B/de not_active IP Right Cessation
- 1970-04-10 CA CA079,859A patent/CA974995A/en not_active Expired
- 1970-04-10 DE DE19702017265 patent/DE2017265A1/de active Pending
- 1970-04-10 NL NL7005191A patent/NL7005191A/xx unknown
- 1970-04-10 FR FR7013077A patent/FR2042321B1/fr not_active Expired
- 1970-04-10 DE DE19702017255 patent/DE2017255A1/de active Pending
- 1970-04-10 FR FR707013078A patent/FR2042322B1/fr not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2723091A1 (fr) * | 1994-07-29 | 1996-02-02 | Esteve Labor Dr | Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles |
| WO1996004287A1 (fr) * | 1994-07-29 | 1996-02-15 | Laboratorios Del Dr. Esteve, S.A. | Tetrahydropyridine-(ou 4-hydroxypiperidine) alkylazoles ayant une activite pour les recepteurs sigma et/ou 5ht1a |
| US5731331A (en) * | 1994-07-29 | 1998-03-24 | Laboratorios Del Dr. Esteve, S.A. | Tetrahydropyridine-(or 4-hydroxypiperidine) alkylazoles |
| US6355659B1 (en) | 1994-07-29 | 2002-03-12 | Laboratorios Del Dr. Esteve, S.A. | 4-(4-Chlorophenyl)-1236-tetrahydro-1(1H-124-triazol-1-yl)butty)pyrideine and salts thereof; pharmaceutical compositions and method of treating psychoses utilizing same |
| WO1996004250A1 (en) * | 1994-08-05 | 1996-02-15 | Pfizer Inc. | Benzimidazole derivatives having dopaminergic activity |
| AU703431B2 (en) * | 1994-08-05 | 1999-03-25 | Pfizer Inc. | Benzimidazole derivatives having dopaminergic activity |
| US5883094A (en) * | 1995-04-24 | 1999-03-16 | Pfizer Inc. | Benzimidazolone derivatives with central dopaminergic activity |
| US5889010A (en) * | 1995-05-18 | 1999-03-30 | Pfizer Inc. | Benzimidazole derivatives having dopaminergic activity |
Also Published As
| Publication number | Publication date |
|---|---|
| US3647790A (en) | 1972-03-07 |
| NL7005191A (en16) | 1970-10-13 |
| US3634441A (en) | 1972-01-11 |
| FR2042322B1 (en16) | 1973-06-08 |
| GB1289089A (en16) | 1972-09-13 |
| FR2042321B1 (en16) | 1974-03-22 |
| FR2042322A1 (en16) | 1971-02-12 |
| BE748392A (fr) | 1970-09-16 |
| CH549038A (de) | 1974-05-15 |
| DE2017255A1 (de) | 1970-10-08 |
| SE366040B (en16) | 1974-04-08 |
| CH556336A (de) | 1974-11-29 |
| US3644414A (en) | 1972-02-22 |
| FR2042321A1 (en16) | 1971-02-12 |
| GB1299621A (en) | 1972-12-13 |
| CA974995A (en) | 1975-09-23 |
| US3635982A (en) | 1972-01-18 |
| AT294815B (de) | 1971-12-10 |
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