NO830042L - 4-difenylmetyl-1-((oxoalkyl)imino)metyl-piperidiner og derivater derav. - Google Patents

4-difenylmetyl-1-((oxoalkyl)imino)metyl-piperidiner og derivater derav.

Info

Publication number: NO830042L
Authority: NO; Norway
Prior art keywords: methyl; acid; imino; diphenylmethyl; piperidine
Prior art date: 1982-02-02

Application number

NO830042A

Other languages

English (en)

Norwegian (no)

Inventor

Malcolm Keith Scott

Original Assignee

Mcneilab Inc

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.)

1982-02-02

Filing date

1983-01-07

Publication date

1983-08-03

1983-01-07 Application filed by Mcneilab Inc filed Critical Mcneilab Inc

1983-08-03 Publication of NO830042L publication Critical patent/NO830042L/no

Links

-1 IMINO Chemical class 0.000 title description 3
101000740162 Homo sapiens Sodium- and chloride-dependent transporter XTRP3 Proteins 0.000 title 1
102100037189 Sodium- and chloride-dependent transporter XTRP3 Human genes 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 35
239000002253 acid Substances 0.000 claims description 29
238000000034 method Methods 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
239000012458 free base Substances 0.000 claims description 7
LNSWILOGIZECFQ-UHFFFAOYSA-N 8-[(4-benzhydrylpiperidin-1-yl)methylideneamino]octan-2-one Chemical compound C1CN(C=NCCCCCCC(=O)C)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 LNSWILOGIZECFQ-UHFFFAOYSA-N 0.000 claims description 3
125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
125000005188 oxoalkyl group Chemical group 0.000 claims description 3
REGDQFLMEUPLNG-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-[6-(2-methyl-1,3-dioxolan-2-yl)hexyl]methanimine Chemical compound C1CC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C=NCCCCCCC1(C)OCCO1 REGDQFLMEUPLNG-UHFFFAOYSA-N 0.000 claims description 2
OOHPMNYAILKCMV-UHFFFAOYSA-N 1-[(4-benzhydrylpiperidin-1-yl)methylideneamino]propan-2-one Chemical compound C1CN(C=NCC(=O)C)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 OOHPMNYAILKCMV-UHFFFAOYSA-N 0.000 claims 1
KIGQNWOOYHMSJP-UHFFFAOYSA-N 10-[(4-benzhydrylpiperidin-1-yl)methylideneamino]decan-2-one Chemical compound C1CN(C=NCCCCCCCCC(=O)C)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 KIGQNWOOYHMSJP-UHFFFAOYSA-N 0.000 claims 1
NMUCGASDIVPPNF-UHFFFAOYSA-N 8-[(4-benzhydrylpiperidin-1-yl)methylideneamino]octan-2-ol Chemical compound C1CN(C=NCCCCCCC(O)C)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 NMUCGASDIVPPNF-UHFFFAOYSA-N 0.000 claims 1
YXVLSWZNPIIZNR-UHFFFAOYSA-N n-[8-[(4-benzhydrylpiperidin-1-yl)methylideneamino]octan-2-ylidene]hydroxylamine Chemical compound C1CN(C=NCCCCCCC(C)=NO)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 YXVLSWZNPIIZNR-UHFFFAOYSA-N 0.000 claims 1
230000027119 gastric acid secretion Effects 0.000 abstract description 6
230000005764 inhibitory process Effects 0.000 abstract description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
239000000243 solution Substances 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
238000004519 manufacturing process Methods 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
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238000012360 testing method Methods 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 5
239000010502 orange oil Substances 0.000 description 5
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
235000019502 Orange oil Nutrition 0.000 description 4
150000001409 amidines Chemical class 0.000 description 4
239000003826 tablet Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UNVKOTIRSRODTD-UHFFFAOYSA-N 6-(2-methyl-1,3-dioxolan-2-yl)hexan-1-amine Chemical compound NCCCCCCC1(C)OCCO1 UNVKOTIRSRODTD-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 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
239000003937 drug carrier Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
210000004051 gastric juice Anatomy 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000005245 sintering Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
CKHACJQHTLEVBI-UHFFFAOYSA-N 2-(7-oxooctyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCCCC(=O)C)C(=O)C2=C1 CKHACJQHTLEVBI-UHFFFAOYSA-N 0.000 description 2
IHQJXDLHKZENCY-UHFFFAOYSA-N 4-benzhydrylpiperidine-1-carbaldehyde Chemical compound C1CN(C=O)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 IHQJXDLHKZENCY-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-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
150000001241 acetals Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 2
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 2
WQWJAPIRSZZBRI-UHFFFAOYSA-N ethyl 2-acetyl-7-(1,3-dioxoisoindol-2-yl)heptanoate Chemical compound C1=CC=C2C(=O)N(CCCCCC(C(=O)OCC)C(C)=O)C(=O)C2=C1 WQWJAPIRSZZBRI-UHFFFAOYSA-N 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
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 2
150000002576 ketones Chemical group 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
HPYKRLQBMUPOFA-UHFFFAOYSA-N piperidin-1-ylmethanimine Chemical class N=CN1CCCCC1 HPYKRLQBMUPOFA-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000000746 purification Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000013049 sediment Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
KHVGUXUSDXHEMC-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-[(2-methyl-1,3-dioxolan-2-yl)methyl]methanimine Chemical compound C1CC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C=NCC1(C)OCCO1 KHVGUXUSDXHEMC-UHFFFAOYSA-N 0.000 description 1
KHFFLMUXVPHZNB-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-[8-(2-methyl-1,3-dioxolan-2-yl)octyl]methanimine Chemical compound C1CC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C=NCCCCCCCCC1(C)OCCO1 KHFFLMUXVPHZNB-UHFFFAOYSA-N 0.000 description 1
JXPCRJDMUSNASY-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-octylmethanimine Chemical compound C1CN(C=NCCCCCCCC)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 JXPCRJDMUSNASY-UHFFFAOYSA-N 0.000 description 1
QKVHAKICMNABGB-UHFFFAOYSA-N 2-(5-bromopentyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCCBr)C(=O)C2=C1 QKVHAKICMNABGB-UHFFFAOYSA-N 0.000 description 1
ZTCDCMLNXHCGHC-UHFFFAOYSA-N 2-[6-(2-methyl-1,3-dioxolan-2-yl)hexyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCCCCC1(C)OCCO1 ZTCDCMLNXHCGHC-UHFFFAOYSA-N 0.000 description 1
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
KLMAKAFPRKBGQL-UHFFFAOYSA-N 8-[(4-benzhydrylpiperidin-1-yl)methylideneamino]octan-2-ol;naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21.C1CN(C=NCCCCCCC(O)C)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 KLMAKAFPRKBGQL-UHFFFAOYSA-N 0.000 description 1
NDLGJJAZYYJQOB-UHFFFAOYSA-N 8-[(4-benzhydrylpiperidin-1-yl)methylideneamino]octan-2-one;sulfuric acid Chemical compound OS(O)(=O)=O.C1CN(C=NCCCCCCC(=O)C)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 NDLGJJAZYYJQOB-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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239000005909 Kieselgur Substances 0.000 description 1
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125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
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239000011260 aqueous acid Substances 0.000 description 1
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SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
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WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
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KKEIAWKQIBIEQN-UHFFFAOYSA-N naphthalene-2-sulfonic acid;piperidine Chemical compound C1CCNCC1.C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KKEIAWKQIBIEQN-UHFFFAOYSA-N 0.000 description 1
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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
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
230000001175 peptic effect Effects 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000013223 sprague-dawley female rat Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000002731 stomach secretion inhibitor Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid 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
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- C07D209/49—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters
- 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
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical 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)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

NO830042A 1982-02-02 1983-01-07 4-difenylmetyl-1-((oxoalkyl)imino)metyl-piperidiner og derivater derav. NO830042L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/345,128 US4370335A (en)	1982-02-02	1982-02-02	Antisecretory 4-diphenylmethyl-1-[(oxoalkyl)imino]methyl-piperidines and their derivatives

Publications (1)

Publication Number	Publication Date
NO830042L true NO830042L (no)	1983-08-03

Family

ID=23353650

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO830042A NO830042L (no)	1982-02-02	1983-01-07	4-difenylmetyl-1-((oxoalkyl)imino)metyl-piperidiner og derivater derav.

Country Status (14)

Country	Link
US (1)	US4370335A (es)
EP (1)	EP0087853B1 (es)
JP (1)	JPS58146564A (es)
KR (1)	KR840003251A (es)
AT (1)	ATE19512T1 (es)
AU (1)	AU552804B2 (es)
DE (1)	DE3363208D1 (es)
DK (1)	DK7983A (es)
ES (1)	ES8402820A1 (es)
FI (1)	FI830105L (es)
IL (1)	IL67674A0 (es)
NO (1)	NO830042L (es)
PH (1)	PH17775A (es)
ZA (1)	ZA83109B (es)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4528293A (en) *	1983-10-11	1985-07-09	Mcneilab, Inc.	Heteroaromatic derivatives of iminomethyl piperidines and use to inhibit gastric acid secretion
US4594351A (en) *	1983-10-11	1986-06-10	Mcneilab, Inc.	Furan or thiophene derivatives of iminomethyl piperidines and use to inhibit gastric secretion
JP5463055B2 (ja) *	2009-02-27	2014-04-09	公益財団法人相模中央化学研究所	フタルイミド誘導体及びそれらの製造方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE794596A (fr) *	1972-01-28	1973-05-16	Richardson Merrell Inc	Piperidinoalcanone-oximes substituees et leur procede de preparation
US3946022A (en) *	1974-03-04	1976-03-23	Richardson-Merrell Inc.	Piperidine derivatives
FR2314179A1 (fr) *	1975-06-12	1977-01-07	Ile De France	Nouvelles enamines et leur procede de preparation
US4251655A (en) *	1978-03-29	1981-02-17	Mcneilab, Inc.	Substituted N-iminomethylpiperidines

1982
- 1982-02-02 US US06/345,128 patent/US4370335A/en not_active Expired - Lifetime
1983
- 1983-01-07 ZA ZA83109A patent/ZA83109B/xx unknown
- 1983-01-07 NO NO830042A patent/NO830042L/no unknown
- 1983-01-07 PH PH28361A patent/PH17775A/en unknown
- 1983-01-10 DK DK7983A patent/DK7983A/da not_active Application Discontinuation
- 1983-01-11 ES ES518881A patent/ES8402820A1/es not_active Expired
- 1983-01-12 FI FI830105A patent/FI830105L/fi not_active Application Discontinuation
- 1983-01-12 IL IL67674A patent/IL67674A0/xx unknown
- 1983-01-13 AT AT83300168T patent/ATE19512T1/de not_active IP Right Cessation
- 1983-01-13 EP EP83300168A patent/EP0087853B1/en not_active Expired
- 1983-01-13 DE DE8383300168T patent/DE3363208D1/de not_active Expired
- 1983-01-21 KR KR1019830000234A patent/KR840003251A/ko not_active Application Discontinuation
- 1983-01-28 AU AU10862/83A patent/AU552804B2/en not_active Ceased
- 1983-01-31 JP JP58013031A patent/JPS58146564A/ja active Pending

Also Published As

Publication number	Publication date
AU1086283A (en)	1983-08-11
DK7983A (da)	1983-08-03
FI830105L (fi)	1983-08-03
DE3363208D1 (en)	1986-06-05
ES518881A0 (es)	1984-03-01
US4370335A (en)	1983-01-25
EP0087853A3 (en)	1983-10-05
DK7983D0 (da)	1983-01-10
IL67674A0 (en)	1983-05-15
EP0087853A2 (en)	1983-09-07
AU552804B2 (en)	1986-06-19
PH17775A (en)	1984-12-11
KR840003251A (ko)	1984-08-20
ATE19512T1 (de)	1986-05-15
ES8402820A1 (es)	1984-03-01
EP0087853B1 (en)	1986-04-30
ZA83109B (en)	1984-08-29
JPS58146564A (ja)	1983-09-01
FI830105A0 (fi)	1983-01-12

Publication	Publication Date	Title
US4042700A (en)	1977-08-16	Quaternary N-β-substituted N-alkyl-nortropine benzilates
IE53274B1 (en)	1988-09-28	Chemical compounds derived from cyclobutene
NO171453B (no)	1992-12-07	Fremgangsmaate for fremstilling av krystallinsk paroxetin-hydroklorid-hemihydrat
NO163816B (no)	1990-04-17	Analogifremgangsmaate for fremstilling av nye, terapeutiskaktive piperazinderivater.
US4145427A (en)	1979-03-20	N- 1-(3-Benzoyl-propyl)-4-piperidyl!-sulfonic acid amides and salts thereof
US4490527A (en)	1984-12-25	Benzo-fused heterocyclic anti-ulcer agents
KR860000931B1 (ko)	1986-07-19	궤양 치료제인 2-구아니디노-4-(2-치환된-아미노-4-이미다졸릴)-티아졸의 제조방법
NO812529L (no)	1982-01-25	Analogifremgangsmaate for fremstilling av terapeutisk aktive dibenzo-diazepin-derivater
NO830042L (no)	1983-08-03	4-difenylmetyl-1-((oxoalkyl)imino)metyl-piperidiner og derivater derav.
US3882236A (en)	1975-05-06	Pharmaceutical compositions containing substituted 2-oxo-indolines and the use thereof to treat anxiety and tension
DK149625B (da)	1986-08-18	Analogifremgangsmaade til fremstilling af n-substituerede (8-halogen- eller -trifluormethyl-4-quinolylamino)-benzamider eller et farmaceutiskacceptabelt syreadditionssalt deraf
EP0073645B1 (en)	1986-11-12	2-cyclic amino-2-(1,2-benzisoxazol-3-yl)acetic acid ester derivatives, process for the preparation thereof and composition containing the same
US3974285A (en)	1976-08-10	10,11-Furo-derivatives of cyproheptadine
EP0223512B1 (en)	1992-07-08	2-pyridylacetic acid derivative, preparation process thereof and pharmaceutical composition containing the same
NO117887B (es)	1969-10-06
NO155056B (no)	1986-10-27	Sprengstoff.
US3894032A (en)	1975-07-08	10,11-Furo derivatives of cyproheptadine
US4044143A (en)	1977-08-23	10,11-Bis-(hydroxyalkyl) derivatives of cyproheptadine
US4032640A (en)	1977-06-28	4H-Benzo[4,5]cyclohepta[1,2-b]thiophenes
IE52010B1 (en)	1987-05-13	Naphthyridine derivatives
NO133448B (es)	1976-01-26
US4321382A (en)	1982-03-23	2-Amino-11b-aryl-benzo[a]quinolizines
CA1087193A (en)	1980-10-07	2- (dimethylamino)(3-pyridyl)methyl -cyclohexanol and related compounds
NO791026L (no)	1979-10-02	Substituerte n-iminometylpiperidiner
CA1147329A (en)	1983-05-31	N.sub.b-quaternary derivatives of ajmaline and isoajmaline, methods and intermediate products in the manufacture of their derivatives and method of using same and pharmaceutical compositions thereof