CA1278792C - Antipsychotic fused-ring pyridinylpiperazine derivatives - Google Patents
Antipsychotic fused-ring pyridinylpiperazine derivativesInfo
- Publication number
- CA1278792C CA1278792C CA000503794A CA503794A CA1278792C CA 1278792 C CA1278792 C CA 1278792C CA 000503794 A CA000503794 A CA 000503794A CA 503794 A CA503794 A CA 503794A CA 1278792 C CA1278792 C CA 1278792C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- piperazinyl
- butyl
- pyridin
- 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 - Fee Related
Links
- 230000000561 anti-psychotic effect Effects 0.000 title claims abstract description 19
- GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical class C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 151
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 238000006073 displacement reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 238000007910 systemic administration Methods 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- LIODOFLHMDNDLV-UHFFFAOYSA-N 1,1-dioxo-2-[4-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)butyl]-1,2-benzothiazol-3-one Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCN1CCN(C=2C=3C=CSC=3C=CN=2)CC1 LIODOFLHMDNDLV-UHFFFAOYSA-N 0.000 claims 1
- JYRILLRJWNGMQR-UHFFFAOYSA-N 1-[4-(4-furo[3,2-c]pyridin-4-ylpiperazin-1-yl)butyl]-4,4-dimethylpiperidine-2,6-dione Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2C=3C=COC=3C=CN=2)CC1 JYRILLRJWNGMQR-UHFFFAOYSA-N 0.000 claims 1
- ZJYWNDXQKAEZJP-UHFFFAOYSA-N 1-[4-[4-(2-bromothieno[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]-4,4-dimethylpiperidine-2,6-dione Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2C=3C=C(Br)SC=3C=CN=2)CC1 ZJYWNDXQKAEZJP-UHFFFAOYSA-N 0.000 claims 1
- RUENTAABOQZLLF-UHFFFAOYSA-N 3-[4-(4-thieno[2,3-c]pyridin-7-ylpiperazin-1-yl)butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound O=C1N(CCCCN2CCN(CC2)C=2C=3SC=CC=3C=CN=2)C(=O)SC21CCCC2 RUENTAABOQZLLF-UHFFFAOYSA-N 0.000 claims 1
- OCBRWFLMBAUWCG-UHFFFAOYSA-N 3-[4-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound O=C1N(CCCCN2CCN(CC2)C=2C=3C=CSC=3C=CN=2)C(=O)SC21CCCC2 OCBRWFLMBAUWCG-UHFFFAOYSA-N 0.000 claims 1
- ORDSVYXFMRRIFU-UHFFFAOYSA-N 3-[4-[4-(1-methylpyrrolo[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound N1=CC=C2N(C)C=CC2=C1N(CC1)CCN1CCCCN(C1=O)C(=O)SC21CCCC2 ORDSVYXFMRRIFU-UHFFFAOYSA-N 0.000 claims 1
- FGRXOPGLGIJRPW-UHFFFAOYSA-N 3-[4-[4-(2-methylthieno[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound N1=CC=C2SC(C)=CC2=C1N(CC1)CCN1CCCCN(C1=O)C(=O)SC21CCCC2 FGRXOPGLGIJRPW-UHFFFAOYSA-N 0.000 claims 1
- LLHFTQKVWCXGPI-UHFFFAOYSA-N 4,4-dimethyl-1-[4-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)butyl]piperidine-2,6-dione Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2C=3C=CSC=3C=CN=2)CC1 LLHFTQKVWCXGPI-UHFFFAOYSA-N 0.000 claims 1
- GMZNQMSZVPCDLB-UHFFFAOYSA-N 4,4-dimethyl-1-[4-[4-(1-methylpyrrolo[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]piperidine-2,6-dione Chemical compound N1=CC=C2N(C)C=CC2=C1N(CC1)CCN1CCCCN1C(=O)CC(C)(C)CC1=O GMZNQMSZVPCDLB-UHFFFAOYSA-N 0.000 claims 1
- RLIZPUXPCGFMOI-UHFFFAOYSA-N 4,4-dimethyl-1-[4-[4-(2-methylfuro[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]piperidine-2,6-dione Chemical compound N1=CC=C2OC(C)=CC2=C1N(CC1)CCN1CCCCN1C(=O)CC(C)(C)CC1=O RLIZPUXPCGFMOI-UHFFFAOYSA-N 0.000 claims 1
- QBICJHHCQYFVMI-UHFFFAOYSA-N 4-[4-(4-furo[3,2-c]pyridin-4-ylpiperazin-1-yl)butyl]morpholine-3,5-dione Chemical compound O=C1COCC(=O)N1CCCCN1CCN(C=2C=3C=COC=3C=CN=2)CC1 QBICJHHCQYFVMI-UHFFFAOYSA-N 0.000 claims 1
- UFCKXALAMVSRPD-UHFFFAOYSA-N 4-[4-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)butyl]morpholine-3,5-dione Chemical compound O=C1COCC(=O)N1CCCCN1CCN(C=2C=3C=CSC=3C=CN=2)CC1 UFCKXALAMVSRPD-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- MXAJVDHGJCYEKL-UHFFFAOYSA-N morpholine-3,5-dione Chemical compound O=C1COCC(=O)N1 MXAJVDHGJCYEKL-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 18
- 125000002619 bicyclic group Chemical group 0.000 abstract description 7
- 125000001424 substituent group Chemical group 0.000 abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 5
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 abstract description 5
- 229940123464 Thiazolidinedione Drugs 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 150000001467 thiazolidinediones Chemical class 0.000 abstract description 2
- 239000003420 antiserotonin agent Substances 0.000 abstract 1
- IJSMDZFKMKEIRX-UHFFFAOYSA-N morpholine-2,6-dione Chemical class O=C1CNCC(=O)O1 IJSMDZFKMKEIRX-UHFFFAOYSA-N 0.000 abstract 1
- 229940125670 thienopyridine Drugs 0.000 abstract 1
- 239000002175 thienopyridine Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 19
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- 238000006243 chemical reaction Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 229910001868 water Inorganic materials 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
- 239000003176 neuroleptic agent Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 208000009132 Catalepsy Diseases 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 206010047853 Waxy flexibility Diseases 0.000 description 10
- 230000000506 psychotropic effect Effects 0.000 description 10
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- -1 heterocyclic carbon compounds Chemical class 0.000 description 9
- 230000000701 neuroleptic effect Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000164 antipsychotic agent Substances 0.000 description 6
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
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- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73120185A | 1985-05-06 | 1985-05-06 | |
| US731,201 | 1985-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1278792C true CA1278792C (en) | 1991-01-08 |
Family
ID=24938510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000503794A Expired - Fee Related CA1278792C (en) | 1985-05-06 | 1986-03-11 | Antipsychotic fused-ring pyridinylpiperazine derivatives |
Country Status (25)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5801186A (en) | 1987-11-20 | 1998-09-01 | Hoechst Marion Roussel, Inc. | 3- 4-(1-substituted-4-piperazinyl)butyl!-4-thiazolidinone and related compounds |
| US4880930A (en) * | 1987-11-30 | 1989-11-14 | New James S | Psychotropic acyclic amide derivatives |
| US4780466A (en) * | 1988-03-17 | 1988-10-25 | Hoechst-Roussel Pharmaceuticals, Inc. | Arylpiperazinylalkoxy derivatives of cyclic imides |
| IE903410A1 (en) * | 1989-10-09 | 1991-04-10 | Novo Nordisk As | Indole derivatives, their preparation and use |
| US5272148A (en) * | 1992-09-09 | 1993-12-21 | Hoechst-Roussel Pharmaceuticals Incorporated | Heteroarenylpiperazines |
| FR2738822B1 (fr) * | 1995-09-15 | 1997-10-31 | Synthelabo | Derives de 4-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)quinolein-2(1h)-one, leur preparation et leur application en therapeutique |
| IL123600A (en) * | 1995-09-15 | 2001-05-20 | Sanofi Synthelabo | History of quinolone - 2 (1H), their preparation and pharmaceutical preparations containing them |
| FR2738823B1 (fr) * | 1995-09-15 | 1997-10-31 | Synthelabo | Derives de 3-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)-3,4-dihydroquinolein-2(1h)-one,leur preparation et leur application en therapeutique |
| FR2738824B1 (fr) * | 1995-09-15 | 1997-10-31 | Synthelabo | Derives de 3-(omega(4-(thieno(3,2-c)pyridin-4-yl)piperazin-1 -yl)alkyl)-3,4-dihydroquinazolin-2(1h)-one,leur preparation et leur application en therapeutique |
| FR2761071B1 (fr) * | 1997-03-20 | 1999-12-03 | Synthelabo | Derives de quinolein-2(1h)-one et de dihydroquinolein-2(1h)- one, leur preparation et leur application en therapeutique |
| FR2797874B1 (fr) * | 1999-08-27 | 2002-03-29 | Adir | Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US20040077605A1 (en) | 2001-06-20 | 2004-04-22 | Salvati Mark E. | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4367335A (en) * | 1981-08-03 | 1983-01-04 | Mead Johnson & Company | Thiazolidinylalkylene piperazine derivatives |
| US4452799A (en) * | 1981-12-23 | 1984-06-05 | Mead Johnson & Company | Benzisothiazole and benzisoxazole piperazine derivatives |
| US4361565A (en) * | 1981-12-28 | 1982-11-30 | Mead Johnson & Company | 2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyridines |
-
1986
- 1986-03-11 CA CA000503794A patent/CA1278792C/en not_active Expired - Fee Related
- 1986-03-19 ZA ZA862046A patent/ZA862046B/xx unknown
- 1986-04-29 EG EG250/86A patent/EG18206A/xx active
- 1986-04-29 GR GR861149A patent/GR861149B/el unknown
- 1986-04-29 AU AU56795/86A patent/AU593244B2/en not_active Expired
- 1986-04-30 FI FI861820A patent/FI85484C/fi not_active IP Right Cessation
- 1986-05-02 KR KR1019860003445A patent/KR940000829B1/ko not_active Expired - Fee Related
- 1986-05-02 GB GB08610810A patent/GB2174703B/en not_active Expired
- 1986-05-05 CN CN86103071A patent/CN1017901B/zh not_active Expired
- 1986-05-05 NL NL8601146A patent/NL8601146A/nl active Search and Examination
- 1986-05-05 IE IE119386A patent/IE59201B1/en not_active IP Right Cessation
- 1986-05-05 SE SE8602061A patent/SE465270B/sv not_active IP Right Cessation
- 1986-05-05 ES ES554659A patent/ES8801250A1/es not_active Expired
- 1986-05-05 CH CH1830/86A patent/CH672787A5/de not_active IP Right Cessation
- 1986-05-05 LU LU86421A patent/LU86421A1/fr unknown
- 1986-05-05 DE DE3615180A patent/DE3615180C2/de not_active Expired - Lifetime
- 1986-05-05 FR FR8606471A patent/FR2581385B1/fr not_active Expired - Lifetime
- 1986-05-05 DK DK207186A patent/DK165745C/da not_active IP Right Cessation
- 1986-05-05 BE BE0/216623A patent/BE904724A/fr not_active IP Right Cessation
- 1986-05-06 PT PT82523A patent/PT82523B/pt unknown
- 1986-05-06 HU HU861860A patent/HU195509B/hu unknown
- 1986-05-06 JP JP61103726A patent/JPH0753728B2/ja not_active Expired - Lifetime
- 1986-05-06 AT AT0121486A patent/AT398572B/de not_active IP Right Cessation
- 1986-05-06 IT IT8620313A patent/IT1208607B/it active
-
1987
- 1987-09-25 ES ES557757A patent/ES8802149A1/es not_active Expired
- 1987-10-01 MY MYPI87002712A patent/MY100777A/en unknown
-
1988
- 1988-01-28 ES ES557809A patent/ES8802614A1/es not_active Expired
- 1988-05-26 ES ES557839A patent/ES8900138A1/es not_active Expired
- 1988-11-16 ES ES557855A patent/ES8900253A1/es not_active Expired
-
1989
- 1989-02-27 ES ES557865A patent/ES9000005A1/es not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |