GB1580227A - Piperazine derivatives - Google Patents
Piperazine derivatives Download PDFInfo
- Publication number
- GB1580227A GB1580227A GB52038/77A GB5203877A GB1580227A GB 1580227 A GB1580227 A GB 1580227A GB 52038/77 A GB52038/77 A GB 52038/77A GB 5203877 A GB5203877 A GB 5203877A GB 1580227 A GB1580227 A GB 1580227A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperazin
- propane
- carbonyloxy
- compound
- xanthene
- 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
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title claims description 12
- 150000004885 piperazines Chemical class 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 47
- -1 polymethyleneimino substituent Polymers 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 7
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 7
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- BNIBUAVXPXWJHR-UHFFFAOYSA-N propyl 9h-xanthene-9-carboxylate Chemical compound C1=CC=C2C(C(=O)OCCC)C3=CC=CC=C3OC2=C1 BNIBUAVXPXWJHR-UHFFFAOYSA-N 0.000 claims description 6
- PZIBVWUXWNYTNL-UHFFFAOYSA-N 1-(3-methoxyphenyl)piperazine Chemical compound COC1=CC=CC(N2CCNCC2)=C1 PZIBVWUXWNYTNL-UHFFFAOYSA-N 0.000 claims description 5
- YKSVXVKIYYQWBB-UHFFFAOYSA-N 1-butylpiperazine Chemical compound CCCCN1CCNCC1 YKSVXVKIYYQWBB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- PTJSLCXRMMGRLY-UHFFFAOYSA-N 1-(2-phenoxyethyl)piperazine Chemical compound C=1C=CC=CC=1OCCN1CCNCC1 PTJSLCXRMMGRLY-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 15
- HKHVOAWFHWULQC-UHFFFAOYSA-N propyl 9H-xanthene-9-carboxylate dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C(C(=O)OCCC)C3=CC=CC=C3OC2=C1 HKHVOAWFHWULQC-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- KGMXPXPXPAAUMD-UHFFFAOYSA-N propane;dihydrochloride Chemical compound Cl.Cl.CCC KGMXPXPXPAAUMD-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 230000003288 anthiarrhythmic effect Effects 0.000 description 4
- 230000000916 dilatatory effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- YRIFWVMRUFKWLM-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)piperazine Chemical compound CC1=CC=C(C)C(N2CCNCC2)=C1 YRIFWVMRUFKWLM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003416 antiarrhythmic agent Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000013849 propane Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LOJCUYCKDGYLJH-UHFFFAOYSA-N 1-(3-phenylpropyl)piperazine Chemical compound C=1C=CC=CC=1CCCN1CCNCC1 LOJCUYCKDGYLJH-UHFFFAOYSA-N 0.000 description 2
- OVEVYSWOILUFMF-UHFFFAOYSA-N 1-[(3,4,5-trimethoxyphenyl)methyl]piperazine Chemical compound COC1=C(OC)C(OC)=CC(CN2CCNCC2)=C1 OVEVYSWOILUFMF-UHFFFAOYSA-N 0.000 description 2
- ZWAQJGHGPPDZSF-UHFFFAOYSA-N 1-prop-2-enylpiperazine Chemical compound C=CCN1CCNCC1 ZWAQJGHGPPDZSF-UHFFFAOYSA-N 0.000 description 2
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- DECNYCSJSYBABP-UHFFFAOYSA-N 2-methyl-1-(4-methylphenyl)piperazine Chemical compound CC1CNCCN1C1=CC=C(C)C=C1 DECNYCSJSYBABP-UHFFFAOYSA-N 0.000 description 2
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 2
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C07D295/04—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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes 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 in position 9
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Anesthesiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU76RI605A HU174215B (hu) | 1976-12-15 | 1976-12-15 | Sposob poluchenija novykh proizvodnykh piperazina i kislotnykh additivnykh i chetvjortichnykh solej |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1580227A true GB1580227A (en) | 1980-11-26 |
Family
ID=11001009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB52038/77A Expired GB1580227A (en) | 1976-12-15 | 1977-12-14 | Piperazine derivatives |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US4140790A (enExample) |
| JP (2) | JPS6026114B2 (enExample) |
| AT (1) | AT359507B (enExample) |
| BE (1) | BE861849A (enExample) |
| CA (1) | CA1080219A (enExample) |
| CH (1) | CH632750A5 (enExample) |
| DE (1) | DE2755707A1 (enExample) |
| ES (1) | ES465061A1 (enExample) |
| FI (1) | FI65427C (enExample) |
| FR (1) | FR2374322A1 (enExample) |
| GB (1) | GB1580227A (enExample) |
| HU (1) | HU174215B (enExample) |
| IL (1) | IL53552A (enExample) |
| IN (1) | IN146474B (enExample) |
| NL (1) | NL7713827A (enExample) |
| NO (1) | NO147306C (enExample) |
| PT (1) | PT67403B (enExample) |
| SE (1) | SE430159B (enExample) |
| SU (1) | SU694071A3 (enExample) |
| YU (1) | YU293677A (enExample) |
| ZA (1) | ZA777398B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU174215B (hu) * | 1976-12-15 | 1979-11-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh proizvodnykh piperazina i kislotnykh additivnykh i chetvjortichnykh solej |
| US4703120A (en) * | 1986-04-28 | 1987-10-27 | Ortho Pharmaceutical Corporation | Furo(3,4-d)pyrimidine-2,4-dione derivatives and intermediates thereof |
| CN1060168C (zh) * | 1994-05-06 | 2001-01-03 | 中国人民解放军军事医学科学院毒物药物研究所 | 新的呫吨衍生物，其制备方法及含它们的药物组合物 |
| CN1625555A (zh) | 2002-02-01 | 2005-06-08 | 阿斯特拉曾尼卡有限公司 | 喹唑啉化合物 |
| JP2006522742A (ja) * | 2003-04-08 | 2006-10-05 | ニューロームド テクノロジーズ、インク． | ピペラジンから距離をおいて配置したベンズヒドリル基から成る一群のカルシウムチャンネル阻害剤 |
| US20080207738A1 (en) * | 2007-02-28 | 2008-08-28 | Cancure Laboratories, Llc | Drug combinations to treat drug resistant tumors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3481930A (en) * | 1966-11-21 | 1969-12-02 | American Home Prod | Xanthene and thioxanthene-9 ureas and propionamides |
| US3502662A (en) * | 1968-03-18 | 1970-03-24 | American Home Prod | N-(9-xanthenyl or thioxanthenyl)-3-amino or iodo-propionamides and 4-(9-xanthenyl or thioxanthenyl)-thiosemicarbazones |
| FR2201084B1 (enExample) * | 1972-09-29 | 1975-10-31 | Bouchara Emile | |
| GB1437868A (en) * | 1973-05-09 | 1976-06-03 | Synthelabo | Arylpiperazinoalkyl esters |
| HU174215B (hu) * | 1976-12-15 | 1979-11-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh proizvodnykh piperazina i kislotnykh additivnykh i chetvjortichnykh solej |
-
1976
- 1976-12-15 HU HU76RI605A patent/HU174215B/hu unknown
-
1977
- 1977-11-25 JP JP52140843A patent/JPS6026114B2/ja not_active Expired
- 1977-12-02 CH CH1475877A patent/CH632750A5/de not_active IP Right Cessation
- 1977-12-05 AT AT867677A patent/AT359507B/de not_active IP Right Cessation
- 1977-12-06 IL IL53552A patent/IL53552A/xx unknown
- 1977-12-07 SE SE7713906A patent/SE430159B/xx unknown
- 1977-12-09 FR FR7737196A patent/FR2374322A1/fr active Granted
- 1977-12-12 US US05/859,928 patent/US4140790A/en not_active Expired - Lifetime
- 1977-12-12 YU YU02936/77A patent/YU293677A/xx unknown
- 1977-12-12 IN IN1717/CAL/77A patent/IN146474B/en unknown
- 1977-12-12 FI FI773743A patent/FI65427C/fi not_active IP Right Cessation
- 1977-12-12 ZA ZA00777398A patent/ZA777398B/xx unknown
- 1977-12-13 SU SU772555706A patent/SU694071A3/ru active
- 1977-12-14 CA CA293,096A patent/CA1080219A/en not_active Expired
- 1977-12-14 JP JP14945477A patent/JPS5377073A/ja active Pending
- 1977-12-14 GB GB52038/77A patent/GB1580227A/en not_active Expired
- 1977-12-14 ES ES465061A patent/ES465061A1/es not_active Expired
- 1977-12-14 BE BE183452A patent/BE861849A/xx not_active IP Right Cessation
- 1977-12-14 NL NL7713827A patent/NL7713827A/xx not_active Application Discontinuation
- 1977-12-14 DE DE19772755707 patent/DE2755707A1/de not_active Ceased
- 1977-12-14 NO NO774294A patent/NO147306C/no unknown
- 1977-12-14 PT PT67403A patent/PT67403B/pt unknown
-
1978
- 1978-12-28 US US05/974,082 patent/US4250310A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| YU293677A (en) | 1982-08-31 |
| NO147306B (no) | 1982-12-06 |
| FR2374322A1 (fr) | 1978-07-13 |
| IL53552A0 (en) | 1978-03-10 |
| FI65427B (fi) | 1984-01-31 |
| ZA777398B (en) | 1978-10-25 |
| NO147306C (no) | 1983-03-16 |
| PT67403B (en) | 1979-05-21 |
| CA1080219A (en) | 1980-06-24 |
| AT359507B (de) | 1980-11-10 |
| IN146474B (enExample) | 1979-06-16 |
| JPS6026114B2 (ja) | 1985-06-21 |
| BE861849A (fr) | 1978-03-31 |
| NO774294L (no) | 1978-06-16 |
| SE7713906L (sv) | 1978-06-16 |
| SU694071A3 (ru) | 1979-10-25 |
| FI65427C (fi) | 1984-05-10 |
| US4140790A (en) | 1979-02-20 |
| PT67403A (en) | 1978-01-01 |
| IL53552A (en) | 1981-07-31 |
| JPS5377073A (en) | 1978-07-08 |
| JPS5377080A (en) | 1978-07-08 |
| NL7713827A (nl) | 1978-06-19 |
| HU174215B (hu) | 1979-11-28 |
| ES465061A1 (es) | 1979-01-01 |
| SE430159B (sv) | 1983-10-24 |
| ATA867677A (de) | 1980-04-15 |
| US4250310A (en) | 1981-02-10 |
| FR2374322B1 (enExample) | 1981-11-27 |
| FI773743A7 (fi) | 1978-06-16 |
| DE2755707A1 (de) | 1978-06-29 |
| CH632750A5 (de) | 1982-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |