CA1077941A - Piperidine derivatives of indole - Google Patents
Piperidine derivatives of indoleInfo
- Publication number
- CA1077941A CA1077941A CA264,610A CA264610A CA1077941A CA 1077941 A CA1077941 A CA 1077941A CA 264610 A CA264610 A CA 264610A CA 1077941 A CA1077941 A CA 1077941A
- Authority
- CA
- Canada
- Prior art keywords
- indole
- ethyl
- piperidino
- piperidine
- process according
- 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
- 150000003053 piperidines Chemical class 0.000 title claims abstract description 14
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims abstract description 10
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title claims abstract description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- -1 3-{2-[4-(2-bromophenoxymethyl)-piperidino]-ethyl}-indole Chemical compound 0.000 claims description 53
- 239000000126 substance Substances 0.000 claims description 22
- NTLAICDKHHQUGC-UHFFFAOYSA-N 3-(2-bromoethyl)-1h-indole Chemical compound C1=CC=C2C(CCBr)=CNC2=C1 NTLAICDKHHQUGC-UHFFFAOYSA-N 0.000 claims description 18
- BREBKAKBNYXIOP-UHFFFAOYSA-N 4-(phenoxymethyl)piperidine Chemical compound C1CNCCC1COC1=CC=CC=C1 BREBKAKBNYXIOP-UHFFFAOYSA-N 0.000 claims description 7
- KBLJGGVCECDLEX-UHFFFAOYSA-N 3-[2-[4-(phenoxymethyl)piperidin-1-yl]ethyl]-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CCN(CC1)CCC1COC1=CC=CC=C1 KBLJGGVCECDLEX-UHFFFAOYSA-N 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- GCSMDZLKHPZCIM-UHFFFAOYSA-N 1-methyl-3-[2-[4-(phenoxymethyl)piperidin-1-yl]ethyl]indole Chemical compound C12=CC=CC=C2N(C)C=C1CCN(CC1)CCC1COC1=CC=CC=C1 GCSMDZLKHPZCIM-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 150000002475 indoles Chemical class 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- GKDOBWORFYLTIL-UHFFFAOYSA-N 3-(2-bromoethyl)-2-methyl-1h-indole Chemical compound C1=CC=C2C(CCBr)=C(C)NC2=C1 GKDOBWORFYLTIL-UHFFFAOYSA-N 0.000 claims description 2
- FGIVWTSVLVUKOK-UHFFFAOYSA-N 4-[(2-bromophenoxy)methyl]piperidine Chemical compound BrC1=CC=CC=C1OCC1CCNCC1 FGIVWTSVLVUKOK-UHFFFAOYSA-N 0.000 claims description 2
- XYROETVBSCXMHN-UHFFFAOYSA-N 4-[(2-butoxyphenoxy)methyl]piperidine Chemical compound CCCCOC1=CC=CC=C1OCC1CCNCC1 XYROETVBSCXMHN-UHFFFAOYSA-N 0.000 claims description 2
- YEDQERJRGLCJKY-UHFFFAOYSA-N 4-[(2-chlorophenoxy)methyl]piperidine Chemical compound ClC1=CC=CC=C1OCC1CCNCC1 YEDQERJRGLCJKY-UHFFFAOYSA-N 0.000 claims description 2
- GTYCVCKSMFWBQA-UHFFFAOYSA-N 4-[(2-fluorophenoxy)methyl]piperidine Chemical compound FC1=CC=CC=C1OCC1CCNCC1 GTYCVCKSMFWBQA-UHFFFAOYSA-N 0.000 claims description 2
- CCZZNPBXUZCPEZ-UHFFFAOYSA-N 4-[(2-methoxyphenoxy)methyl]piperidine Chemical compound COC1=CC=CC=C1OCC1CCNCC1 CCZZNPBXUZCPEZ-UHFFFAOYSA-N 0.000 claims description 2
- BJWGYFBJEZCOEG-UHFFFAOYSA-N 4-[(3-methoxyphenoxy)methyl]piperidine Chemical compound COC1=CC=CC(OCC2CCNCC2)=C1 BJWGYFBJEZCOEG-UHFFFAOYSA-N 0.000 claims description 2
- IGXCLKXDHNOUIB-UHFFFAOYSA-N 4-[(3-methylphenoxy)methyl]piperidine Chemical compound CC1=CC=CC(OCC2CCNCC2)=C1 IGXCLKXDHNOUIB-UHFFFAOYSA-N 0.000 claims description 2
- KWLNQJLKIFFYNF-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]piperidine Chemical compound C1=CC(Cl)=CC=C1OCC1CCNCC1 KWLNQJLKIFFYNF-UHFFFAOYSA-N 0.000 claims description 2
- RERPCSOKGBHYNQ-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]piperidine Chemical compound C1=CC(F)=CC=C1OCC1CCNCC1 RERPCSOKGBHYNQ-UHFFFAOYSA-N 0.000 claims description 2
- NPWGQYGFHRSCQA-UHFFFAOYSA-N 4-[(4-methoxyphenoxy)methyl]piperidine Chemical compound C1=CC(OC)=CC=C1OCC1CCNCC1 NPWGQYGFHRSCQA-UHFFFAOYSA-N 0.000 claims description 2
- OIRBFUKKCSYAKX-UHFFFAOYSA-N 4-[(4-methylphenoxy)methyl]piperidine Chemical compound C1=CC(C)=CC=C1OCC1CCNCC1 OIRBFUKKCSYAKX-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- MERTXFWGALCWFT-UHFFFAOYSA-N 3-(1h-indol-3-yl)propyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCCC1=CNC2=CC=CC=C12 MERTXFWGALCWFT-UHFFFAOYSA-N 0.000 claims 1
- GGGKTMYGNHOBHF-UHFFFAOYSA-N 3-(2-bromoethyl)-1-methylindole Chemical compound C1=CC=C2N(C)C=C(CCBr)C2=C1 GGGKTMYGNHOBHF-UHFFFAOYSA-N 0.000 claims 1
- PVLZQVJPOZTGMJ-UHFFFAOYSA-N 4-[(2-methylphenoxy)methyl]piperidine Chemical compound CC1=CC=CC=C1OCC1CCNCC1 PVLZQVJPOZTGMJ-UHFFFAOYSA-N 0.000 claims 1
- JRKWHWMRJYOIEA-UHFFFAOYSA-N 4-[(3-chlorophenoxy)methyl]piperidine Chemical compound ClC1=CC=CC(OCC2CCNCC2)=C1 JRKWHWMRJYOIEA-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 2
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000243 solution Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000008298 dragée Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000006243 chemical reaction Methods 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
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- 229940057948 magnesium stearate Drugs 0.000 description 3
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- 235000010981 methylcellulose Nutrition 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229920000945 Amylopectin Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 206010067482 No adverse event Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 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
- 229940095064 tartrate Drugs 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
- 238000011282 treatment Methods 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
- 235000019871 vegetable fat Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752550001 DE2550001A1 (de) | 1975-11-07 | 1975-11-07 | Neue indol-derivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077941A true CA1077941A (en) | 1980-05-20 |
Family
ID=5961169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA264,610A Expired CA1077941A (en) | 1975-11-07 | 1976-10-28 | Piperidine derivatives of indole |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5259164A (Direct) |
| AT (1) | AT352727B (Direct) |
| BE (1) | BE847975A (Direct) |
| CA (1) | CA1077941A (Direct) |
| DE (1) | DE2550001A1 (Direct) |
| DK (1) | DK141529C (Direct) |
| FI (1) | FI763150A7 (Direct) |
| FR (1) | FR2330396A1 (Direct) |
| GB (1) | GB1510765A (Direct) |
| IE (1) | IE43972B1 (Direct) |
| LU (1) | LU76143A1 (Direct) |
| NL (1) | NL7612288A (Direct) |
| SE (1) | SE7612236L (Direct) |
| SU (1) | SU628816A3 (Direct) |
| ZA (1) | ZA766379B (Direct) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2905876A1 (de) | 1979-02-16 | 1980-08-28 | Boehringer Mannheim Gmbh | Neue piperidinopropylderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4327103A (en) * | 1980-07-07 | 1982-04-27 | Hoechst-Roussel Pharmaceuticals Incorporated | 3-{3-[4-(4-Fluorobenzoyl)piperidyl]propyl}-2-methyl indole |
-
1975
- 1975-11-07 DE DE19752550001 patent/DE2550001A1/de not_active Withdrawn
-
1976
- 1976-10-25 ZA ZA766379A patent/ZA766379B/xx unknown
- 1976-10-28 CA CA264,610A patent/CA1077941A/en not_active Expired
- 1976-10-29 IE IE2396/76A patent/IE43972B1/en unknown
- 1976-11-02 SU SU762415646A patent/SU628816A3/ru active
- 1976-11-02 DK DK495076A patent/DK141529C/da active
- 1976-11-03 FI FI763150A patent/FI763150A7/fi not_active Application Discontinuation
- 1976-11-03 SE SE7612236A patent/SE7612236L/ not_active Application Discontinuation
- 1976-11-04 GB GB45918/76A patent/GB1510765A/en not_active Expired
- 1976-11-04 BE BE172070A patent/BE847975A/xx unknown
- 1976-11-05 AT AT823976A patent/AT352727B/de not_active IP Right Cessation
- 1976-11-05 FR FR7633391A patent/FR2330396A1/fr active Granted
- 1976-11-05 LU LU76143A patent/LU76143A1/xx unknown
- 1976-11-05 JP JP51133141A patent/JPS5259164A/ja active Pending
- 1976-11-05 NL NL7612288A patent/NL7612288A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IE43972B1 (en) | 1981-07-15 |
| SE7612236L (sv) | 1977-05-08 |
| DE2550001A1 (de) | 1977-05-12 |
| ATA823976A (de) | 1979-03-15 |
| DK141529B (da) | 1980-04-14 |
| BE847975A (fr) | 1977-05-04 |
| GB1510765A (en) | 1978-05-17 |
| FR2330396B1 (Direct) | 1979-06-29 |
| NL7612288A (nl) | 1977-05-10 |
| LU76143A1 (Direct) | 1977-05-18 |
| JPS5259164A (en) | 1977-05-16 |
| IE43972L (en) | 1977-05-07 |
| SU628816A3 (ru) | 1978-10-15 |
| AT352727B (de) | 1979-10-10 |
| FI763150A7 (Direct) | 1977-05-08 |
| FR2330396A1 (fr) | 1977-06-03 |
| DK141529C (da) | 1980-09-01 |
| DK495076A (da) | 1977-05-08 |
| ZA766379B (en) | 1977-10-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |