DK169325B1 - Analogifremgangsmåde til fremstilling af N-heterocyclyl-4-piperidinaminer - Google Patents
Analogifremgangsmåde til fremstilling af N-heterocyclyl-4-piperidinaminer Download PDFInfo
- Publication number
- DK169325B1 DK169325B1 DK129879A DK129879A DK169325B1 DK 169325 B1 DK169325 B1 DK 169325B1 DK 129879 A DK129879 A DK 129879A DK 129879 A DK129879 A DK 129879A DK 169325 B1 DK169325 B1 DK 169325B1
- Authority
- DK
- Denmark
- Prior art keywords
- parts
- group
- methyl
- piperidinyl
- benzimidazol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 15
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- 239000000376 reactant Substances 0.000 claims description 3
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- 239000000543 intermediate Substances 0.000 description 35
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- 229960001701 chloroform Drugs 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 229910052799 carbon Inorganic materials 0.000 description 27
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 27
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- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- UUBJKHVFGWGJKX-UHFFFAOYSA-N hydrate tetrahydrochloride Chemical compound O.Cl.Cl.Cl.Cl UUBJKHVFGWGJKX-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
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- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- YCDPBTSAQFQAOG-UHFFFAOYSA-N methyl 4-(1h-benzimidazol-2-ylamino)-3-methylpiperidine-1-carboxylate Chemical compound CC1CN(C(=O)OC)CCC1NC1=NC2=CC=CC=C2N1 YCDPBTSAQFQAOG-UHFFFAOYSA-N 0.000 description 1
- IEGKYTVBMCRSHJ-UHFFFAOYSA-N methyl 4-[[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]amino]-3-methylpiperidine-1-carboxylate Chemical compound CC1CN(C(=O)OC)CCC1NC1=NC2=CC=CC=C2N1CC1=CC=C(F)C=C1 IEGKYTVBMCRSHJ-UHFFFAOYSA-N 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- RXEDATWQBKXUNH-UHFFFAOYSA-N n,1-dibenzyl-n-[1-(2-phenylethyl)piperidin-4-yl]benzimidazol-2-amine Chemical compound C1CC(N(CC=2C=CC=CC=2)C=2N(C3=CC=CC=C3N=2)CC=2C=CC=CC=2)CCN1CCC1=CC=CC=C1 RXEDATWQBKXUNH-UHFFFAOYSA-N 0.000 description 1
- NTQFSYCNLNWKED-UHFFFAOYSA-N n-(1-cyclohexylpiperidin-4-yl)-1-[(4-fluorophenyl)methyl]benzimidazol-2-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2N=C1NC1CCN(C2CCCCC2)CC1 NTQFSYCNLNWKED-UHFFFAOYSA-N 0.000 description 1
- AIAAAKULVUIAJT-UHFFFAOYSA-N n-(1-methylpiperidin-4-yl)-1-phenylbenzimidazol-2-amine Chemical compound C1CN(C)CCC1NC1=NC2=CC=CC=C2N1C1=CC=CC=C1 AIAAAKULVUIAJT-UHFFFAOYSA-N 0.000 description 1
- QXEIPXZZVSYYKU-UHFFFAOYSA-N n-[1-(2-phenylethyl)piperidin-4-yl]-n-propan-2-yl-1h-benzimidazol-2-amine Chemical compound N=1C2=CC=CC=C2NC=1N(C(C)C)C(CC1)CCN1CCC1=CC=CC=C1 QXEIPXZZVSYYKU-UHFFFAOYSA-N 0.000 description 1
- PZYLEZXDWSQMAI-UHFFFAOYSA-N n-[1-(2-phenylethyl)piperidin-4-yl]-n-propyl-1h-benzimidazol-2-amine Chemical compound N=1C2=CC=CC=C2NC=1N(CCC)C(CC1)CCN1CCC1=CC=CC=C1 PZYLEZXDWSQMAI-UHFFFAOYSA-N 0.000 description 1
- NORHEQUXRGEKPS-UHFFFAOYSA-N n-[1-[2-(1h-benzimidazol-2-ylamino)ethyl]piperidin-4-yl]-1-[(4-fluorophenyl)methyl]benzimidazol-2-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2N=C1NC1CCN(CCNC=2NC3=CC=CC=C3N=2)CC1 NORHEQUXRGEKPS-UHFFFAOYSA-N 0.000 description 1
- NUJYKVDVUYYGQC-UHFFFAOYSA-N n-[1-[2-(dibenzylamino)ethyl]piperidin-4-yl]-1-[(4-fluorophenyl)methyl]benzimidazol-2-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2N=C1NC1CCN(CCN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)CC1 NUJYKVDVUYYGQC-UHFFFAOYSA-N 0.000 description 1
- FTYLPBZGFLTPHT-UHFFFAOYSA-N n-benzyl-1-[(2-chlorophenyl)methyl]-n-[1-(2-phenylethyl)piperidin-4-yl]benzimidazol-2-amine Chemical compound ClC1=CC=CC=C1CN1C2=CC=CC=C2N=C1N(C1CCN(CCC=2C=CC=CC=2)CC1)CC1=CC=CC=C1 FTYLPBZGFLTPHT-UHFFFAOYSA-N 0.000 description 1
- BRAJXEKWXWWLEG-UHFFFAOYSA-N n-benzyl-1-[(2-methoxyphenyl)methyl]-n-[1-(2-phenylethyl)piperidin-4-yl]benzimidazol-2-amine Chemical compound COC1=CC=CC=C1CN1C2=CC=CC=C2N=C1N(C1CCN(CCC=2C=CC=CC=2)CC1)CC1=CC=CC=C1 BRAJXEKWXWWLEG-UHFFFAOYSA-N 0.000 description 1
- KHPMFONMQZYCMG-UHFFFAOYSA-N n-benzyl-1-[(4-fluorophenyl)methyl]-n-[1-(2-phenylethyl)piperidin-4-yl]benzimidazol-2-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2N=C1N(C1CCN(CCC=2C=CC=CC=2)CC1)CC1=CC=CC=C1 KHPMFONMQZYCMG-UHFFFAOYSA-N 0.000 description 1
- ASEUGHCETOYURJ-UHFFFAOYSA-N n-benzyl-1-[(4-methylphenyl)methyl]-n-[1-(2-phenylethyl)piperidin-4-yl]benzimidazol-2-amine Chemical compound C1=CC(C)=CC=C1CN1C2=CC=CC=C2N=C1N(C1CCN(CCC=2C=CC=CC=2)CC1)CC1=CC=CC=C1 ASEUGHCETOYURJ-UHFFFAOYSA-N 0.000 description 1
- MDDAUMFFPCLRQD-UHFFFAOYSA-N n-benzyl-1-ethyl-n-[1-(2-phenylethyl)piperidin-4-yl]benzimidazol-2-amine Chemical compound N=1C2=CC=CC=C2N(CC)C=1N(C1CCN(CCC=2C=CC=CC=2)CC1)CC1=CC=CC=C1 MDDAUMFFPCLRQD-UHFFFAOYSA-N 0.000 description 1
- FXMPPQGQNSTUGE-UHFFFAOYSA-N n-benzyl-1h-benzimidazol-2-amine Chemical class N=1C2=CC=CC=C2NC=1NCC1=CC=CC=C1 FXMPPQGQNSTUGE-UHFFFAOYSA-N 0.000 description 1
- QGGSAXFVVSPELW-UHFFFAOYSA-N n-benzyl-n-[1-(2-phenylethyl)piperidin-4-yl]-1h-benzimidazol-2-amine Chemical compound C1CC(N(CC=2C=CC=CC=2)C=2NC3=CC=CC=C3N=2)CCN1CCC1=CC=CC=C1 QGGSAXFVVSPELW-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- JGWUVCVDDDKXLW-UHFFFAOYSA-N n-cyclopropyl-n-[1-(2-phenylethyl)piperidin-4-yl]-1h-benzimidazol-2-amine Chemical compound C1CC(N(C2CC2)C=2NC3=CC=CC=C3N=2)CCN1CCC1=CC=CC=C1 JGWUVCVDDDKXLW-UHFFFAOYSA-N 0.000 description 1
- UQYJDWQGPULEOJ-UHFFFAOYSA-N n-ethyl-n-[1-(2-phenylethyl)piperidin-4-yl]-1h-benzimidazol-2-amine Chemical compound N=1C2=CC=CC=C2NC=1N(CC)C(CC1)CCN1CCC1=CC=CC=C1 UQYJDWQGPULEOJ-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229940075559 piperine Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/54—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK083183A DK171841B1 (da) | 1978-04-03 | 1983-02-24 | N-hetero-cyclyl-4-piperidinaminer |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89253478A | 1978-04-03 | 1978-04-03 | |
| US89253478 | 1978-04-03 | ||
| US06/002,276 US4219559A (en) | 1979-01-10 | 1979-01-10 | N-Heterocyclyl-4-piperidinamines |
| US227679 | 1979-01-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK129879A DK129879A (da) | 1979-10-04 |
| DK169325B1 true DK169325B1 (da) | 1994-10-10 |
Family
ID=26670178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK129879A DK169325B1 (da) | 1978-04-03 | 1979-03-29 | Analogifremgangsmåde til fremstilling af N-heterocyclyl-4-piperidinaminer |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP0005318B1 (enExample) |
| JP (2) | JPS54151982A (enExample) |
| AT (1) | AT373887B (enExample) |
| AU (1) | AU523352B2 (enExample) |
| BG (1) | BG38164A3 (enExample) |
| CA (1) | CA1140119A (enExample) |
| CS (1) | CS256358B2 (enExample) |
| CY (1) | CY1250A (enExample) |
| DE (1) | DE2961740D1 (enExample) |
| DK (1) | DK169325B1 (enExample) |
| EG (1) | EG13913A (enExample) |
| ES (1) | ES479206A1 (enExample) |
| FI (1) | FI64801C (enExample) |
| GR (1) | GR64907B (enExample) |
| HK (1) | HK3184A (enExample) |
| HU (1) | HU182965B (enExample) |
| IE (1) | IE47818B1 (enExample) |
| IL (1) | IL56992A (enExample) |
| MY (1) | MY8500046A (enExample) |
| NO (2) | NO154058C (enExample) |
| NZ (1) | NZ189978A (enExample) |
| PH (1) | PH15877A (enExample) |
| PL (1) | PL123380B1 (enExample) |
| PT (1) | PT69429A (enExample) |
| RO (1) | RO79320A (enExample) |
| SG (1) | SG29883G (enExample) |
| SU (1) | SU1056902A3 (enExample) |
| YU (2) | YU42484B (enExample) |
| ZA (1) | ZA791557B (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA19091A1 (fr) * | 1980-03-10 | 1981-10-01 | Janssen Pharmaceutica Nv | Nouveaux derives de i-(4-aryl-cyclohexyl)piperidine . |
| IN156065B (enExample) * | 1982-07-12 | 1985-05-04 | Janssen Pharmaceutica Nv | |
| US4556660A (en) * | 1982-07-12 | 1985-12-03 | Janssen Pharmaceutica N.V. | N-(Bicyclic heterocyclyl)-4-piperidinamines |
| US4634704A (en) * | 1983-10-06 | 1987-01-06 | Janssen Pharmaceutica, N.V. | Anti-allergic five membered heterocyclic ring containing N-(bicyclic heterocycyl)-4-piperidinamines |
| EP0144101B1 (en) * | 1983-11-30 | 1991-02-06 | Janssen Pharmaceutica N.V. | Bicyclic heterocyclyl containing n-(bicyclic heterocyclyl)-4-piperidinamines |
| JPS60174778A (ja) * | 1984-01-09 | 1985-09-09 | ジヤンセン・フア−マシユ−チカ・ナ−ムロ−ゼ・フエンノ−トシヤツプ | Ｎ−ヘテロシクリル−４−ピペリジンアミン |
| KR930005004B1 (ko) * | 1985-04-15 | 1993-06-11 | 쟈안센 파아마슈우티카 엔. 부이. | 치환된 n-[(4-피페리디닐)알킬]이환 축합 옥사졸아민 및 티아졸아민의 제조방법 |
| GB8515934D0 (en) * | 1985-06-24 | 1985-07-24 | Janssen Pharmaceutica Nv | (4-piperidinomethyl and-hetero)purines |
| CA1327579C (en) * | 1986-02-03 | 1994-03-08 | Frans Eduard Janssens | Anti-histaminic compositions containing n-heterocyclyl-4-piperidinamines |
| NZ223654A (en) * | 1987-03-09 | 1990-03-27 | Janssen Pharmaceutica Nv | 1-alkyl-substituted-benzimidazole-4-piperidinamines and pharmaceutical compositions |
| FR2618435B1 (fr) * | 1987-07-23 | 1989-10-27 | Synthelabo | Derives de benzimidazole, leur preparation et leur application en therapeutique |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857391A (en) * | 1955-04-15 | 1958-10-21 | Merck & Co Inc | Aminomethylbenzimidazoles |
| US2971005A (en) * | 1958-10-17 | 1961-02-07 | Merck & Co Inc | Nu-substituted derivatives of 2-benzylaminobenzimidazoles |
| BE788065A (fr) * | 1971-08-26 | 1973-02-26 | Degussa | Nouvelles aza-benzimidazoles et procede pour leur preparation |
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1979
- 1979-03-19 CA CA000323763A patent/CA1140119A/en not_active Expired
- 1979-03-21 AU AU45296/79A patent/AU523352B2/en not_active Expired
- 1979-03-23 NZ NZ189978A patent/NZ189978A/en unknown
- 1979-03-29 DK DK129879A patent/DK169325B1/da not_active IP Right Cessation
- 1979-03-29 GR GR58721A patent/GR64907B/el unknown
- 1979-03-30 EP EP79300525A patent/EP0005318B1/en not_active Expired
- 1979-03-30 RO RO7997082A patent/RO79320A/ro unknown
- 1979-03-30 CY CY1250A patent/CY1250A/xx unknown
- 1979-03-30 DE DE7979300525T patent/DE2961740D1/de not_active Expired
- 1979-04-01 EG EG200/79A patent/EG13913A/xx active
- 1979-04-02 AT AT0242579A patent/AT373887B/de not_active IP Right Cessation
- 1979-04-02 ZA ZA791557A patent/ZA791557B/xx unknown
- 1979-04-02 FI FI791084A patent/FI64801C/fi not_active IP Right Cessation
- 1979-04-02 JP JP3844779A patent/JPS54151982A/ja active Granted
- 1979-04-02 ES ES479206A patent/ES479206A1/es not_active Expired
- 1979-04-02 CS CS792227A patent/CS256358B2/cs unknown
- 1979-04-02 IL IL56992A patent/IL56992A/xx unknown
- 1979-04-02 NO NO791097A patent/NO154058C/no unknown
- 1979-04-03 PH PH22344A patent/PH15877A/en unknown
- 1979-04-03 SU SU792747000A patent/SU1056902A3/ru active
- 1979-04-03 PL PL1979214648A patent/PL123380B1/pl unknown
- 1979-04-03 PT PT69429A patent/PT69429A/pt unknown
- 1979-04-03 BG BG043114A patent/BG38164A3/xx unknown
- 1979-04-03 HU HU79JA841A patent/HU182965B/hu unknown
- 1979-04-03 YU YU784/79A patent/YU42484B/xx unknown
- 1979-08-08 IE IE676/79A patent/IE47818B1/en not_active IP Right Cessation
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1983
- 1983-03-02 YU YU502/83A patent/YU43158B/xx unknown
- 1983-05-26 SG SG298/83A patent/SG29883G/en unknown
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1984
- 1984-01-12 HK HK31/84A patent/HK3184A/en not_active IP Right Cessation
- 1984-06-25 NO NO842563A patent/NO154090C/no unknown
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1985
- 1985-12-30 MY MY46/85A patent/MY8500046A/xx unknown
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1988
- 1988-06-14 JP JP63144898A patent/JPH01117880A/ja active Granted
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| Date | Code | Title | Description |
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| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |