PL147092B1 - Process for preparing novel n-/bicycloheterocyclo/-4-piperidinamines - Google Patents

Process for preparing novel n-/bicycloheterocyclo/-4-piperidinamines Download PDF

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Publication number: PL147092B1
Authority: PL; Poland
Prior art keywords: group; formula; lower alkyl; groups; radical
Prior art date: 1982-07-12

Application number

PL24297083A

Other languages

English (en)

Polish (pl)

Other versions

PL242970A1 (en

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date 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 date listed.)

1982-07-12

Filing date

1983-07-12

Publication date

1989-04-29

1983-07-12 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1985-08-13 Publication of PL242970A1 publication Critical patent/PL242970A1/xx

1989-04-29 Publication of PL147092B1 publication Critical patent/PL147092B1/pl

Links

238000004519 manufacturing process Methods 0.000 title 1
-1 alkyl radicals Chemical class 0.000 claims description 96
150000001875 compounds Chemical class 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 47
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
239000002585 base Substances 0.000 claims description 42
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
125000005843 halogen group Chemical group 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
238000000034 method Methods 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 12
150000003254 radicals Chemical class 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
125000003373 pyrazinyl group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
JMTMWFZXOIWTLX-UHFFFAOYSA-N 2-pyridin-2-yloxypyridine Chemical group C=1C=CC=NC=1OC1=CC=CC=N1 JMTMWFZXOIWTLX-UHFFFAOYSA-N 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 50
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 49
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 43
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
239000000203 mixture Substances 0.000 description 30
239000002904 solvent Substances 0.000 description 26
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
241000700159 Rattus Species 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
229920002055 compound 48/80 Polymers 0.000 description 12
239000000047 product Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
239000001257 hydrogen Substances 0.000 description 9
241001465754 Metazoa Species 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 8
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
230000037396 body weight Effects 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
239000000739 antihistaminic agent Substances 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000000725 suspension Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
208000026935 allergic disease Diseases 0.000 description 4
230000001387 anti-histamine Effects 0.000 description 4
239000003420 antiserotonin agent Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229940076279 serotonin Drugs 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
210000002784 stomach Anatomy 0.000 description 4
UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000002775 capsule Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000000969 carrier Substances 0.000 description 3
229960001340 histamine Drugs 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 3
239000007787 solid Substances 0.000 description 3
YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 2
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
230000001079 digestive effect Effects 0.000 description 2
210000005069 ears Anatomy 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
235000013305 food Nutrition 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
210000001156 gastric mucosa Anatomy 0.000 description 2
210000004907 gland Anatomy 0.000 description 2
239000008103 glucose Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
230000003902 lesion Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
239000006187 pill Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000010956 selective crystallization Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
230000035939 shock Effects 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 description 1
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STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
KPJZHOPZRAFDTN-ZRGWGRIASA-N (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)CC)C2)=C3C2=CN(C)C3=C1 KPJZHOPZRAFDTN-ZRGWGRIASA-N 0.000 description 1
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
AXKPFOAXAHJUAG-UHFFFAOYSA-N pipamperone Chemical compound C1CC(C(=O)N)(N2CCCCC2)CCN1CCCC(=O)C1=CC=C(F)C=C1 AXKPFOAXAHJUAG-UHFFFAOYSA-N 0.000 description 1
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 1
125000005936 piperidyl group Chemical group 0.000 description 1
FIADGNVRKBPQEU-UHFFFAOYSA-N pizotifen Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CCC2=C1C=CS2 FIADGNVRKBPQEU-UHFFFAOYSA-N 0.000 description 1
229960004572 pizotifen Drugs 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002265 prevention Effects 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
GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical class NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
230000028327 secretion Effects 0.000 description 1
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
229950001675 spiperone Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 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
230000001225 therapeutic effect Effects 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

PL24297083A 1982-07-12 1983-07-12 Process for preparing novel n-/bicycloheterocyclo/-4-piperidinamines PL147092B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US39762682A	1982-07-12	1982-07-12

Publications (2)

Publication Number	Publication Date
PL242970A1 PL242970A1 (en)	1985-08-13
PL147092B1 true PL147092B1 (en)	1989-04-29

Family

ID=23571984

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL24297083A PL147092B1 (en)	1982-07-12	1983-07-12	Process for preparing novel n-/bicycloheterocyclo/-4-piperidinamines

Country Status (4)

Country	Link
JP (1)	JPS5921680A (zh)
IN (1)	IN156065B (zh)
PL (1)	PL147092B1 (zh)
ZA (1)	ZA835044B (zh)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4888426A (en) *	1983-11-30	1989-12-19	Janssen Pharmaceutica N.V.	1-(5-methyl-furan-2-ylmethyl)-N-(4-piperidinyl)imidazo [4,5-6]pyridine-2-amine
CA1327579C (en) *	1986-02-03	1994-03-08	Frans Eduard Janssens	Anti-histaminic compositions containing n-heterocyclyl-4-piperidinamines
PT650476E (pt) *	1993-04-07	2002-11-29	Otsuka Pharma Co Ltd	Agente vasodilatador periferico que contem derivados n-acilados de 4-amino-piperidina como ingredientes activos
MY142362A (en)	2004-01-29	2010-11-30	Otsuka Pharma Co Ltd	Pharmaceutical composition for promoting angiogenesis
JP5617970B2 (ja) *	2009-02-19	2014-11-05	富士通株式会社	新規化合物、並びに、結合阻害剤、抗アレルギー剤、抗喘息剤、及び抗炎症剤
JP5617969B2 (ja) *	2009-02-19	2014-11-05	富士通株式会社	新規化合物、並びに、結合阻害剤、抗アレルギー剤、抗喘息剤、及び抗炎症剤

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1140119A (en) *	1978-04-03	1983-01-25	Joseph Torremans	N-heterocyclyl-4-piperidinamines

1983
- 1983-05-12 IN IN599/CAL/83A patent/IN156065B/en unknown
- 1983-07-11 ZA ZA835044A patent/ZA835044B/xx unknown
- 1983-07-11 JP JP12490083A patent/JPS5921680A/ja active Pending
- 1983-07-12 PL PL24297083A patent/PL147092B1/pl unknown

Also Published As

Publication number	Publication date
ZA835044B (en)	1985-02-27
JPS5921680A (ja)	1984-02-03
PL242970A1 (en)	1985-08-13
IN156065B (zh)	1985-05-04

Publication	Publication Date	Title
SU1297728A3 (ru)	1987-03-15	Способ получени @ -гетероциклил-4-пиперидинаминов или их фармацевтически приемлемых солей
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KR870001169B1 (ko)	1987-06-15	4-[(두고리 헤테로시클릴)-메틸 및 -헤테로] 피페리딘 유도체의 제조방법
KR100725190B1 (ko)	2007-06-07	4-아미노피페리딘 유도체 및 그의 약제로서의 용도
US20060194807A1 (en)	2006-08-31	Di-aryl substituted pyrazole modulators of metabotropic glutamate receptor-5
JPS6110577A (ja)	1986-01-18	５員複素環式環を含有するｎ−（二環式ヘテロシクリル）−４−ピペリジンアミン類
CS256358B2 (en)	1988-04-15	Method of n-heterocyclyl-4-piperidinamines preparation
US7268151B2 (en)	2007-09-11	Di-aryl substituted triazole modulators of metabotropic glutamate receptor-5
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PL146377B1 (en)	1989-01-31	Method of obtaining novel derivatives 4-piperidinoamine
PL147092B1 (en)	1989-04-29	Process for preparing novel n-/bicycloheterocyclo/-4-piperidinamines
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US5578607A (en)	1996-11-26	6-(2-imidazolinylamino)quinoline compounds useful as alpha-2 adrenoceptor agonists
US4820822A (en)	1989-04-11	Novel N-(bicyclic heterocyclyl)-4-piperidinamines
US4760074A (en)	1988-07-26	Novel-N-(bicyclic heterocyclyl)-4-piperidinamines
USRE33833E (en)	1992-02-25	Novel N-(bicyclic heterocyclyl)-4-piperidinamines
KR880000247B1 (ko)	1988-03-15	4-[(두고리 헤테로시클릴)-메틸 및-헤테로] 피페리딘 유도체의 제조방법
PL146228B1 (en)	1989-01-31	Method of obtaining novel n-/bicyclic heterocyclilo/-4-piperidinamines containing five-member heterocyclic rings
CZ16485A3 (cs)	1993-12-15	Způsob přípravy 4-/(bicyklyl heterocyklyl) methyl a hetero/-piperidinů
JPS60174778A (ja)	1985-09-09	Ｎ−ヘテロシクリル−４−ピペリジンアミン