FI85266B - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1,4-disubstituerade piperazinderivat. - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1,4-disubstituerade piperazinderivat. Download PDFInfo
- Publication number
- FI85266B FI85266B FI871874A FI871874A FI85266B FI 85266 B FI85266 B FI 85266B FI 871874 A FI871874 A FI 871874A FI 871874 A FI871874 A FI 871874A FI 85266 B FI85266 B FI 85266B
- Authority
- FI
- Finland
- Prior art keywords
- group
- general formula
- piperazine
- compound
- ethyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 238000000034 method Methods 0.000 claims abstract description 25
- -1 1,4-disubstituted piperazine Chemical class 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 230000002829 reductive effect Effects 0.000 claims description 12
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 7
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 150000004885 piperazines Chemical class 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 4
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- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 3
- TVJVVUFECOXCEF-UHFFFAOYSA-N 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-prop-2-ynylpiperazine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)OCCN1CCN(CC#C)CC1 TVJVVUFECOXCEF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 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 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
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- 239000003795 chemical substances by application Substances 0.000 claims description 2
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- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 238000005956 quaternization reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
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- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 235000004554 glutamine Nutrition 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
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- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- VUXSPDNLYQTOSY-UHFFFAOYSA-N phenylmercuric borate Chemical compound OB(O)O[Hg]C1=CC=CC=C1 VUXSPDNLYQTOSY-UHFFFAOYSA-N 0.000 description 1
- 229960000247 phenylmercuric borate Drugs 0.000 description 1
- 230000037081 physical activity Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229950001675 spiperone Drugs 0.000 description 1
- 108010092215 spiroperidol receptor Proteins 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229960004479 trihexyphenidyl hydrochloride Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
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- 238000005550 wet granulation Methods 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (2)
1. Förfarande för framställning av nya terapeutiskt använd-bara 1,4-disubstituerade piperazinderivat med den ällinänne formeln (I) O-ICH^-N7 N - Rg R2 I R, r5 4 väri R, , R-, R, och R. är likadana eller olika och st&r för väte eller halogen eller en trihalometyl-, en lägre alkyl-, en lägre alkoxi-, en nitro-, en hydroxyl-, en fenyl-C14-alkyloxi- eller en l-(2-propenyl- 4-piperazinyl)-grupp, Rg representerar väte eller en C1_4-alkylgrupp, Rg stär för en C3_g-alkenyl- eller en -alkynylgrupp och n är 2 eller 3, samt farmaceutiskt acceptable syraadditions- och kvaternära ammoniumsalter därav, kännetecknat av att a) en förening med den allmänna formeln (II) 41 85266 jb^-ά R2 I R< r5 väri R1# R2, R3, R4 och Rg har samma betydelse som ovan och Y representerar en grupp OM (väri M stär för en alkalime-tall, företrädesvis litium, kalium eller natrium eller för en grupp MgHlg, väri Hlg stär för halogen) eller Y representerar en hydroxylgrupp, omsätts med en förening med den allmänna formeln (III) X-(CH2)n-Nf_^<"R6 (III) väri Rg och n har samma betydelse som ovan och X representerar halogen eller en alkylsulfonyloxi- eller en arylsulfonyl-oxigrupp, när Y stär för en grupp OM, eller X representerar halogen eller en hydroxyl-, en alkylsulfonyloxi- eller en arylsulfonyloxigrupp, när Y stär för en hydroxylgrupp, eller b) en förening med den allmänna formeln (IV) *1 Hlg r3 <» r2 I R, vari R^ R2, R3, r4, Rg och Hlg har samma betydelse som ovan, omsätts med ett piperazinderivat med den allmänna formeln (V) 42 85266 Y-(CH2)n-N/ ^^-Rg \—/ (V) väri Rg och n har samma betydelse som ovan och Y represente-rar en hydroxylgrupp eller en grupp OM', väri M' represente-rar en alkalimetall, eller c) en förening med den allmänna formeln (VI) R, 0-(CH2)n-Z r5 vari R1# R2, R3, R4, Rg och n har samma betydelse som ovan och Z stir för halogen eller en alkylsulfonyloxi- eller en arylsulfonyloxigrupp, omsätts med ett piperazinderivat med den allmänna formeln (VII) HN N-Rc (vii) v_/ 6 varl Rg har samma betydelse som ovan, eller d) en förening med den allmänna formeln VIII) 43 8 5266 O — (CH_) -N/ NH
2. N_/ ...... Rs väri R1# R2, R3, R4, Rg och n har sanuna betydelse som ovan, omsätts med en förening med den allmänna formeln (IX) Z - R6 (IX) väri Z och Rg har samma betydelse som ovan, eller e) en förening med den allmänna formeln (I), väri R^, R2, R^, R4, Rg och n har samma betydelse som ovan och Rg stär för en C3g-alkynylgrupp/ reduceras om sä önskas delvis eller helt tili en förening med den allmänna formeln (I), väri Rg representerar en C3_g-alkenylgrupp och R^, R2# R3, R4, Rg och n har samma betydelse som ovan, och, om sä önskas, överförs en sälunda erhällen produkt, som är framställd med nägot av förfarandena a) - e) tili ett syraadditionssalt medelst en organisk eller oorganisk syra eller tili ett kvaternärt ammoniumsalt medelst ett kvater-näriseringsämne eller, om sä önskas, överförs en produkt som är erhällen i formen av ett syraadditionssalt eller ett kvaternärt ammoniumsalt tili motsvarande fria bas, och/eller, om sä önskas, överförs en fri bas till dess syraadditionssalt eller kvaternära ammoniumsalt.
2. Förfarande enligt krav 1, kännetecknat av att man framställer 1-[2-[bis(4-fluorfenylJmetoxi]etyl]-4-(2-propenyl)piperazin, 1-[2-[(3,4-diklorfenyl)fenylmetoxi]etyl]-4-(2-propenyl)-piperazin, 1-[2-[bis(4-fluorfenyl)metoxi]etyl]-4-(2-propynyl)piperazin 44 8 5266 eller dessa föreningars farmaceutiskt acceptable syraadditi-ons- eller kvaternära ammoniumsalter.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU174986 | 1986-04-28 | ||
| HU861749A HU196194B (en) | 1986-04-28 | 1986-04-28 | Process for producing new 1-4 disubstituted piperazines and pharmaceuticals comprising the compounds |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI871874A0 FI871874A0 (fi) | 1987-04-28 |
| FI871874A FI871874A (fi) | 1987-10-29 |
| FI85266B true FI85266B (fi) | 1991-12-13 |
| FI85266C FI85266C (sv) | 1992-03-25 |
Family
ID=10956001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI871874A FI85266C (sv) | 1986-04-28 | 1987-04-28 | Förfarande för framställning av nya terapeutiskt användbara 1,4-disubs tituerade piperazinderivat |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4874765A (sv) |
| EP (1) | EP0243903B1 (sv) |
| JP (1) | JPH0670026B2 (sv) |
| AT (1) | ATE73786T1 (sv) |
| AU (1) | AU599100B2 (sv) |
| CA (1) | CA1308103C (sv) |
| DE (1) | DE3777438D1 (sv) |
| DK (1) | DK213187A (sv) |
| ES (1) | ES2004408A6 (sv) |
| FI (1) | FI85266C (sv) |
| GR (1) | GR870665B (sv) |
| HU (1) | HU196194B (sv) |
| IL (1) | IL82352A0 (sv) |
| ZA (1) | ZA873029B (sv) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU196196B (en) * | 1986-04-28 | 1988-10-28 | Richter Gedeon Vegyeszet | Process for producing new benzhydryl-piperazine derivatives and pharmaceuticals comprising the compounds |
| FR2601366B1 (fr) * | 1986-07-10 | 1988-11-25 | Andre Buzas | Derives de la benzhydryloxyethyl-piperazine, procedes d'obtention et de compositions pharmaceutiques les contenant. |
| DE68903263T2 (de) * | 1988-10-10 | 1993-05-19 | Akzo Nv | Substituierte aromatische verbindungen mit zentraler nervensystem-wirkung. |
| EP0485512A4 (en) * | 1989-08-03 | 1992-08-26 | Us Health | Slowly dissociating (tight binding) dopamine, serotonin or norepinephrine reuptake inhibitors as cocaine, amphetamine and phencyclidine antagonists |
| DK178490D0 (da) * | 1990-07-26 | 1990-07-26 | Novo Nordisk As | 1,4-disubstituerede piperaziner |
| DK178590D0 (da) * | 1990-07-26 | 1990-07-26 | Novo Nordisk As | 1,4-disubstituerede piperaziner |
| US5276035A (en) * | 1990-07-26 | 1994-01-04 | Novo Nordisk A/S | 1,4-disubstituted piperazines |
| SE9202266D0 (sv) * | 1992-07-31 | 1992-07-31 | Kabi Pharmacia Ab | Novel piperazine carboxamides |
| DE19627411A1 (de) * | 1996-07-09 | 1998-01-15 | Bayer Ag | Verfahren zur Decarboxylierung halogenierter aromatischer Carbonsäuren |
| US6743797B2 (en) | 2002-02-22 | 2004-06-01 | Chantest, Inc. | Methods for treating cardiac arrhythmia |
| US20050054010A1 (en) * | 2003-07-15 | 2005-03-10 | Brown Arthur M. | High throughput assay systems and methods for identifying agents that alter surface expression of integral membrane proteins |
| US7211407B2 (en) * | 2003-07-15 | 2007-05-01 | Chan Test, Inc. | High throughput assay systems and methods for identifying agents that alter surface expression of integral membrane proteins |
| US20050208595A1 (en) * | 2004-03-19 | 2005-09-22 | Brown Arthur M | High throughput assay systems and methods for identifying agents that alter expression of cellular proteins |
| EP2671870A1 (en) * | 2012-06-05 | 2013-12-11 | Bioprojet | Novel (aza)benzhydryl ether derivatives, their process of preparation and their use as H4-receptor ligands for therapeutical applications |
| WO2014059367A1 (en) * | 2012-10-11 | 2014-04-17 | Chanrx Corporation | Pharmaceutical compositions containing enantiomerically pure and/or racemic mixtures of chiral piperazine compounds and methods of terminating acute episodes of cardiac arrhythmia, restoring normal sinus rhythm, preventing recurrence of cardiac arrhythmia and maintaining normal sinus rhythm in mammals through administration of said compositions |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE551032A (sv) * | ||||
| BE549420A (sv) * | ||||
| US2988551A (en) * | 1954-07-30 | 1961-06-13 | Union Chimique Belge Sa | Piperazine derivatives |
| GB837986A (en) * | 1956-07-10 | 1960-06-22 | Henri Morren | New piperazine derivatives and process for the preparation thereof |
| JPS50142574A (sv) * | 1974-04-26 | 1975-11-17 | ||
| FR2276824A1 (fr) * | 1974-07-04 | 1976-01-30 | Melon Jean Marie | Derives de la piperazine 1,4-disubstituee, leur procede de preparation et leurs applications therapeutiques |
| GB1545094A (en) * | 1976-12-14 | 1979-05-02 | Gist Brocades Nv | Piperazine derivatives |
| NL8202636A (nl) * | 1982-06-29 | 1984-01-16 | Gist Brocades Nv | Piperazinederivaten, werkwijzen ter bereiding daarvan en farmaceutische preparaten die deze verbindingen bevatten. |
| HU196196B (en) * | 1986-04-28 | 1988-10-28 | Richter Gedeon Vegyeszet | Process for producing new benzhydryl-piperazine derivatives and pharmaceuticals comprising the compounds |
-
1986
- 1986-04-28 HU HU861749A patent/HU196194B/hu not_active IP Right Cessation
-
1987
- 1987-04-22 US US07/041,206 patent/US4874765A/en not_active Expired - Fee Related
- 1987-04-27 DK DK213187A patent/DK213187A/da not_active Application Discontinuation
- 1987-04-28 JP JP62106155A patent/JPH0670026B2/ja not_active Expired - Lifetime
- 1987-04-28 DE DE8787106032T patent/DE3777438D1/de not_active Expired - Fee Related
- 1987-04-28 FI FI871874A patent/FI85266C/sv not_active IP Right Cessation
- 1987-04-28 ES ES8701260A patent/ES2004408A6/es not_active Expired
- 1987-04-28 AU AU72161/87A patent/AU599100B2/en not_active Ceased
- 1987-04-28 AT AT87106032T patent/ATE73786T1/de active
- 1987-04-28 CA CA000535731A patent/CA1308103C/en not_active Expired - Fee Related
- 1987-04-28 EP EP87106032A patent/EP0243903B1/de not_active Expired - Lifetime
- 1987-04-28 ZA ZA873029A patent/ZA873029B/xx unknown
- 1987-04-28 IL IL82352A patent/IL82352A0/xx not_active IP Right Cessation
- 1987-04-28 GR GR870665A patent/GR870665B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL82352A0 (en) | 1987-10-30 |
| AU7216187A (en) | 1987-10-29 |
| DK213187D0 (da) | 1987-04-27 |
| ZA873029B (en) | 1987-10-02 |
| HUT45037A (en) | 1988-05-30 |
| JPS62273969A (ja) | 1987-11-28 |
| FI871874A (fi) | 1987-10-29 |
| ES2004408A6 (es) | 1989-01-01 |
| EP0243903A1 (de) | 1987-11-04 |
| EP0243903B1 (de) | 1992-03-18 |
| HU196194B (en) | 1988-10-28 |
| DK213187A (da) | 1987-10-29 |
| ATE73786T1 (de) | 1992-04-15 |
| CA1308103C (en) | 1992-09-29 |
| US4874765A (en) | 1989-10-17 |
| GR870665B (en) | 1987-09-02 |
| JPH0670026B2 (ja) | 1994-09-07 |
| FI871874A0 (fi) | 1987-04-28 |
| AU599100B2 (en) | 1990-07-12 |
| DE3777438D1 (de) | 1992-04-23 |
| FI85266C (sv) | 1992-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: RICHTER GEDEON VEGYESZETI GYAR RT |