NO309765B1 - Difenylmetylen-piperidin-derivater, anvendelse av og farmasöytiske blandinger inneholdende dem og fremgangsmåte for fremstilling derav - Google Patents

Difenylmetylen-piperidin-derivater, anvendelse av og farmasöytiske blandinger inneholdende dem og fremgangsmåte for fremstilling derav Download PDF

Info

Publication number: NO309765B1
Authority: NO; Norway
Prior art keywords: diphenylmethylene; piperidine; derivative according; piperidine derivative; pharmaceutically acceptable
Prior art date: 1995-07-12

Application number

NO980109A

Other languages

English (en)

Norwegian (no)

Other versions

NO980109L (no

NO980109D0 (no

Inventor

Duncan Robertson Rae

David Robert Jaap

Original Assignee

Akzo Nobel 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.)

1995-07-12

Filing date

1998-01-09

Publication date

2001-03-26

1998-01-09 Application filed by Akzo Nobel Nv filed Critical Akzo Nobel Nv

1998-01-09 Publication of NO980109L publication Critical patent/NO980109L/no

1998-01-09 Publication of NO980109D0 publication Critical patent/NO980109D0/no

2001-03-26 Publication of NO309765B1 publication Critical patent/NO309765B1/no

Links

ZFDDWBKSMIWSBN-UHFFFAOYSA-N 2-benzhydrylidenepiperidine Chemical class N1CCCCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 ZFDDWBKSMIWSBN-UHFFFAOYSA-N 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title description 11
238000000034 method Methods 0.000 title description 5
239000008194 pharmaceutical composition Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 11
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 9
239000003210 dopamine receptor blocking agent Substances 0.000 claims description 5
208000028017 Psychotic disease Diseases 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
238000011321 prophylaxis Methods 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
CLASDMKBOIFHNY-UHFFFAOYSA-N 2-methylidenepiperidine Chemical compound C=C1CCCCN1 CLASDMKBOIFHNY-UHFFFAOYSA-N 0.000 claims description 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
-1 Diphenylethylene piperidine derivative Chemical class 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
241000699670 Mus sp. Species 0.000 description 18
239000000243 solution Substances 0.000 description 18
229960004046 apomorphine Drugs 0.000 description 14
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 12
239000000047 product Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000009194 climbing Effects 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
230000000561 anti-psychotic effect Effects 0.000 description 4
239000013078 crystal Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011541 reaction mixture Substances 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
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
239000012458 free base Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000007920 subcutaneous administration Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
GVPFPFKCQZHWCW-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methylidene]piperidine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)=C1CCNCC1 GVPFPFKCQZHWCW-UHFFFAOYSA-N 0.000 description 2
NLURCGOBHUYBNK-UHFFFAOYSA-N 4-chloro-1-piperidin-1-ylbutan-1-one Chemical compound ClCCCC(=O)N1CCCCC1 NLURCGOBHUYBNK-UHFFFAOYSA-N 0.000 description 2
CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229940121891 Dopamine receptor antagonist Drugs 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
229920004011 Macrolon® Polymers 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
CXWQXGNFZLHLHQ-DPFCLETOSA-N apomorphine hydrochloride Chemical compound [H+].[H+].O.[Cl-].[Cl-].C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3.C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 CXWQXGNFZLHLHQ-DPFCLETOSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000010828 elution Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
235000011087 fumaric acid Nutrition 0.000 description 2
229960002598 fumaric acid Drugs 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 1
WGNUUNAZXFEOKE-UHFFFAOYSA-N 1-tritylpiperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WGNUUNAZXFEOKE-UHFFFAOYSA-N 0.000 description 1
PZYSHLKIRQPGAM-UHFFFAOYSA-N 4-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]-1-pyrrolidin-1-ylbutan-1-one;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)=C1CCN(CCCC(=O)N2CCCC2)CC1 PZYSHLKIRQPGAM-UHFFFAOYSA-N 0.000 description 1
OWZIEPLJGKVJOC-UHFFFAOYSA-N 4-chloro-1-pyrrolidin-1-ylbutan-1-one Chemical compound ClCCCC(=O)N1CCCC1 OWZIEPLJGKVJOC-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
208000009132 Catalepsy Diseases 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
102000015554 Dopamine receptor Human genes 0.000 description 1
108050004812 Dopamine receptor Proteins 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
229920002472 Starch Chemical class 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
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 1
206010047853 Waxy flexibility Diseases 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
230000003097 anti-respiratory effect Effects 0.000 description 1
230000002932 anti-schizophrenic effect Effects 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
229960004365 benzoic acid Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000001913 cellulose Chemical class 0.000 description 1
229920002678 cellulose Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
229960004106 citric acid Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229940052760 dopamine agonists Drugs 0.000 description 1
239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
YBAMRUQHMOWNEU-UHFFFAOYSA-N ethyl 1-tritylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YBAMRUQHMOWNEU-UHFFFAOYSA-N 0.000 description 1
RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
239000007922 nasal spray Substances 0.000 description 1
229940097496 nasal spray Drugs 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
239000006187 pill Substances 0.000 description 1
235000019260 propionic acid Nutrition 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
239000002002 slurry Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Chemical class 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 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
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

NO980109A 1995-07-12 1998-01-09 Difenylmetylen-piperidin-derivater, anvendelse av og farmasöytiske blandinger inneholdende dem og fremgangsmåte for fremstilling derav NO309765B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP95201910		1995-07-12
PCT/EP1996/003099 WO1997003065A1 (en)	1995-07-12	1996-07-09	Diphenylmethylene piperidine derivatives

Publications (3)

Publication Number	Publication Date
NO980109L NO980109L (no)	1998-01-09
NO980109D0 NO980109D0 (no)	1998-01-09
NO309765B1 true NO309765B1 (no)	2001-03-26

Family

ID=8220478

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO980109A NO309765B1 (no)	1995-07-12	1998-01-09	Difenylmetylen-piperidin-derivater, anvendelse av og farmasöytiske blandinger inneholdende dem og fremgangsmåte for fremstilling derav

Country Status (26)

Country	Link
US (1)	US5935974A (cs)
EP (1)	EP0842170B1 (cs)
JP (1)	JPH11508907A (cs)
KR (1)	KR19990028807A (cs)
CN (1)	CN1091108C (cs)
AR (1)	AR003966A1 (cs)
AT (1)	ATE199150T1 (cs)
AU (1)	AU699370B2 (cs)
BR (1)	BR9609330A (cs)
CA (1)	CA2226851A1 (cs)
CZ (1)	CZ288909B6 (cs)
DE (1)	DE69611788T2 (cs)
DK (1)	DK0842170T3 (cs)
ES (1)	ES2156287T3 (cs)
GR (1)	GR3035849T3 (cs)
HU (1)	HUP9802762A3 (cs)
IL (1)	IL118768A (cs)
NO (1)	NO309765B1 (cs)
NZ (1)	NZ315318A (cs)
PL (1)	PL183837B1 (cs)
PT (1)	PT842170E (cs)
RU (1)	RU2162846C2 (cs)
TR (1)	TR199800027T1 (cs)
TW (1)	TW419477B (cs)
WO (1)	WO1997003065A1 (cs)
ZA (1)	ZA965691B (cs)

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CN108884077A (zh)	2016-02-25	2018-11-23	阿森纽荣股份公司	糖苷酶抑制剂
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1996
- 1996-07-01 IL IL11876896A patent/IL118768A/xx not_active IP Right Cessation
- 1996-07-04 ZA ZA965691A patent/ZA965691B/xx unknown
- 1996-07-09 KR KR1019980700107A patent/KR19990028807A/ko not_active Ceased
- 1996-07-09 HU HU9802762A patent/HUP9802762A3/hu unknown
- 1996-07-09 AT AT96927006T patent/ATE199150T1/de not_active IP Right Cessation
- 1996-07-09 PT PT96927006T patent/PT842170E/pt unknown
- 1996-07-09 NZ NZ315318A patent/NZ315318A/en unknown
- 1996-07-09 DE DE69611788T patent/DE69611788T2/de not_active Expired - Fee Related
- 1996-07-09 ES ES96927006T patent/ES2156287T3/es not_active Expired - Lifetime
- 1996-07-09 US US08/983,059 patent/US5935974A/en not_active Expired - Fee Related
- 1996-07-09 PL PL96324451A patent/PL183837B1/pl unknown
- 1996-07-09 WO PCT/EP1996/003099 patent/WO1997003065A1/en not_active Ceased
- 1996-07-09 AU AU66993/96A patent/AU699370B2/en not_active Ceased
- 1996-07-09 RU RU98102392/04A patent/RU2162846C2/ru not_active IP Right Cessation
- 1996-07-09 CZ CZ199883A patent/CZ288909B6/cs not_active IP Right Cessation
- 1996-07-09 BR BR9609330A patent/BR9609330A/pt active Search and Examination
- 1996-07-09 CA CA002226851A patent/CA2226851A1/en not_active Abandoned
- 1996-07-09 EP EP96927006A patent/EP0842170B1/en not_active Expired - Lifetime
- 1996-07-09 TR TR1998/00027T patent/TR199800027T1/xx unknown
- 1996-07-09 DK DK96927006T patent/DK0842170T3/da active
- 1996-07-09 CN CN96195461A patent/CN1091108C/zh not_active Expired - Fee Related
- 1996-07-09 JP JP9505516A patent/JPH11508907A/ja active Pending
- 1996-07-12 AR ARP960103567A patent/AR003966A1/es active IP Right Grant
- 1996-07-29 TW TW085109218A patent/TW419477B/zh not_active IP Right Cessation
1998
- 1998-01-09 NO NO980109A patent/NO309765B1/no unknown
2001
- 2001-05-11 GR GR20010400699T patent/GR3035849T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
CN1190965A (zh)	1998-08-19
HK1010818A1 (en)	1999-07-02
ES2156287T3 (es)	2001-06-16
IL118768A0 (en)	1996-10-31
MX9800368A (es)	1998-03-31
IL118768A (en)	2000-10-31
EP0842170A1 (en)	1998-05-20
NO980109L (no)	1998-01-09
CN1091108C (zh)	2002-09-18
US5935974A (en)	1999-08-10
ATE199150T1 (de)	2001-02-15
DE69611788D1 (de)	2001-03-22
WO1997003065A1 (en)	1997-01-30
PL183837B1 (pl)	2002-07-31
CA2226851A1 (en)	1997-01-30
AU699370B2 (en)	1998-12-03
KR19990028807A (ko)	1999-04-15
DE69611788T2 (de)	2001-08-02
NZ315318A (en)	1999-10-28
EP0842170B1 (en)	2001-02-14
PL324451A1 (en)	1998-05-25
AU6699396A (en)	1997-02-10
HUP9802762A2 (hu)	1999-10-28
HUP9802762A3 (en)	2002-10-28
CZ8398A3 (cs)	1998-06-17
ZA965691B (en)	1997-01-24
RU2162846C2 (ru)	2001-02-10
PT842170E (pt)	2001-06-29
BR9609330A (pt)	1999-05-25
GR3035849T3 (en)	2001-08-31
CZ288909B6 (cs)	2001-09-12
DK0842170T3 (da)	2001-06-18
TR199800027T1 (xx)	1998-05-21
TW419477B (en)	2001-01-21
JPH11508907A (ja)	1999-08-03
AR003966A1 (es)	1998-09-30
NO980109D0 (no)	1998-01-09

Publication	Publication Date	Title
EP0842170B1 (en)	2001-02-14	Diphenylmethylene piperidine derivatives
CA2481461C (en)	2010-01-12	Derivatives of n-[phenyl(piperidin-2-yl) methyl] benzamide, the preparation method thereof and application of same in therapeutics
AU625192B2 (en)	1992-07-02	Piperazine compounds
US3956296A (en)	1976-05-11	1-Substituted-4-benzylpiperidines
HUT53079A (en)	1990-09-28	Process for producing pharmaceutical compositions comprising cyclic amine derivatives as active ingredient and the new active ingredients
HU196370B (en)	1988-11-28	Process for producing piperidine derivatives and pharmaceutical compositions comprising such compounds
BG61120B2 (bg)	1996-11-29	Производни на 1,2,5,6-тетрахидропиридин-3-карбоксалдехид оксим,метод за получаването им,приложението им като лекарствени средства и съдържащите ги състави
JPH0597806A (ja)	1993-04-20	ピペリジン誘導体
US3458521A (en)	1969-07-29	4-phenylpiperidine derivatives
JPS63146874A (ja)	1988-06-18	インドール誘導体
NO146359B (no)	1982-06-07	Analogifremgangsmaate ved fremstilling av terapeutisk aktive cyproheptadinderivater
US4032642A (en)	1977-06-28	1-Substituted-4-benzylpiperidines
DE69404158T2 (de)	1997-10-30	4-alkylamino-1-phenoxyalkyl piperidine als antiinflammatorische, antiallergische und immunomodulierende wirkstoffe
US4650874A (en)	1987-03-17	N-(aralkoxybenzyl)-4(benzhydryl) piperidines
US3743645A (en)	1973-07-03	1-substituted-4-phenoxypiperidines
EP0204309A2 (en)	1986-12-10	Substituted N-benzyl-4(benzhydryl) piperidines
AU607735B2 (en)	1991-03-14	Novel cyclic carbamate derivatives
US20060019995A1 (en)	2006-01-26	2,3-dihydro-4(1H)-pyridone derivatives , method for production thereof and pharmaceutical composition comprising the same
IE49998B1 (en)	1986-01-22	4-(naphthalenyloxy)piperidine derivatives
HK1010818B (en)	2001-05-18	Diphenylmethylene piperidine derivatives
MXPA98000368A (es)	1998-10-15	Derivados de piperidina de difenilmetileno
NO153890B (no)	1986-03-03	Analogifremgangsmaate for fremstilling av terapeutisk aktive piperidinderivater
NO142348B (no)	1980-04-28	Analogifremgangsmaate for fremstilling av farmakologisk aktive 1-(n-(p-fluorbenzoylpropyl)-4-piperidyl)-imidazolidinon-derivater
HUP0004796A2 (hu)	2002-04-29	Antipszichotikus hatású helyettesített piperidinszármazékok, eljárás előállításukra és az ezeket tartalmazó gyógyszerkészítmények
NO761682L (cs)	1976-02-17