NO303448B1 - 1-acylpiperidinforbindelser, deres anvendelse for fremstilling av legemidler samt legemidler inneholdende dem - Google Patents

1-acylpiperidinforbindelser, deres anvendelse for fremstilling av legemidler samt legemidler inneholdende dem Download PDF

Info

Publication number: NO303448B1
Authority: NO; Norway
Prior art keywords: mmol; benzyl; methanol; piperidinamine; formula
Prior art date: 1991-08-12

Application number

NO923123A

Other languages

English (en)

Norwegian (no)

Other versions

NO923123D0 (no

NO923123L (no

Inventor

Walter Schilling

Silvio Ofner

Siem Jacob Veenstra

Original Assignee

Ciba Geigy Ag

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.)

1991-08-12

Filing date

1992-08-11

Publication date

1998-07-13

1992-08-11 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1992-08-11 Publication of NO923123D0 publication Critical patent/NO923123D0/no

1993-02-15 Publication of NO923123L publication Critical patent/NO923123L/no

1998-07-13 Publication of NO303448B1 publication Critical patent/NO303448B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 156
239000003814 drug Substances 0.000 title claims abstract 4
229940079593 drug Drugs 0.000 title claims 2
238000004519 manufacturing process Methods 0.000 title description 3
150000003839 salts Chemical class 0.000 claims abstract description 41
-1 heteroaroyl Chemical group 0.000 claims abstract description 30
239000001257 hydrogen Substances 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 9
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
125000001589 carboacyl group Chemical group 0.000 claims abstract 5
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical group 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000000825 pharmaceutical preparation Substances 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
206010006458 Bronchitis chronic Diseases 0.000 claims description 3
206010010741 Conjunctivitis Diseases 0.000 claims description 3
206010020772 Hypertension Diseases 0.000 claims description 3
208000019695 Migraine disease Diseases 0.000 claims description 3
208000002193 Pain Diseases 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
206010006451 bronchitis Diseases 0.000 claims description 3
208000007451 chronic bronchitis Diseases 0.000 claims description 3
201000004614 iritis Diseases 0.000 claims description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
201000000980 schizophrenia Diseases 0.000 claims description 3
206010009900 Colitis ulcerative Diseases 0.000 claims description 2
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SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
239000004305 biphenyl Substances 0.000 claims description 2
235000010290 biphenyl Nutrition 0.000 claims description 2
125000006267 biphenyl group Chemical group 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
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239000000654 additive Substances 0.000 claims 1
230000036506 anxiety Effects 0.000 claims 1
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125000005493 quinolyl group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 22
239000013543 active substance Substances 0.000 abstract description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 7
QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 abstract description 5
102100024304 Protachykinin-1 Human genes 0.000 abstract description 5
101800003906 Substance P Proteins 0.000 abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
125000005160 aryl oxy alkyl group Chemical group 0.000 abstract description 3
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125000003435 aroyl group Chemical group 0.000 abstract description 2
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125000006254 cycloalkyl carbonyl group Chemical group 0.000 abstract description 2
208000035475 disorder Diseases 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
125000003107 substituted aryl group Chemical group 0.000 abstract 2
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 378
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 355
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 170
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 158
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 108
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 84
229910021529 ammonia Inorganic materials 0.000 description 84
238000000434 field desorption mass spectrometry Methods 0.000 description 81
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 70
235000019439 ethyl acetate Nutrition 0.000 description 50
239000000203 mixture Substances 0.000 description 47
239000007858 starting material Substances 0.000 description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 35
235000002639 sodium chloride Nutrition 0.000 description 35
239000006260 foam Substances 0.000 description 34
239000003921 oil Substances 0.000 description 34
235000019198 oils Nutrition 0.000 description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
239000012074 organic phase Substances 0.000 description 28
229910000033 sodium borohydride Inorganic materials 0.000 description 28
239000012279 sodium borohydride Substances 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
239000002253 acid Substances 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 22
239000000741 silica gel Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
238000000034 method Methods 0.000 description 20
230000002829 reductive effect Effects 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 19
229910052943 magnesium sulfate Inorganic materials 0.000 description 18
235000019341 magnesium sulphate Nutrition 0.000 description 18
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
229910052938 sodium sulfate Inorganic materials 0.000 description 17
235000011152 sodium sulphate Nutrition 0.000 description 17
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239000012458 free base Substances 0.000 description 16
239000003480 eluent Substances 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
235000011114 ammonium hydroxide Nutrition 0.000 description 11
239000002585 base Substances 0.000 description 11
KLDLRDSRCMJKGM-UHFFFAOYSA-N 3-[chloro-(2-oxo-1,3-oxazolidin-3-yl)phosphoryl]-1,3-oxazolidin-2-one Chemical compound C1COC(=O)N1P(=O)(Cl)N1CCOC1=O KLDLRDSRCMJKGM-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
MGCGJBXTNWUHQE-UHFFFAOYSA-N quinoline-4-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CC=NC2=C1 MGCGJBXTNWUHQE-UHFFFAOYSA-N 0.000 description 10
235000011121 sodium hydroxide Nutrition 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
239000012267 brine Substances 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
239000013078 crystal Substances 0.000 description 9
239000005457 ice water Substances 0.000 description 9
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229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
239000000126 substance Substances 0.000 description 9
125000002252 acyl group Chemical group 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
238000000746 purification Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
229910000085 borane Inorganic materials 0.000 description 6
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
238000004090 dissolution Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 6
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QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 5
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239000004480 active ingredient Substances 0.000 description 5
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239000012043 crude product Substances 0.000 description 5
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
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238000005160 1H NMR spectroscopy Methods 0.000 description 3
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YQEJEOMPQPBZCR-GFOWMXPYSA-N [(2r)-4-amino-2-benzylpiperidin-1-yl]-(3,5-dimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C(=O)N2[C@@H](CC(N)CC2)CC=2C=CC=CC=2)=C1 YQEJEOMPQPBZCR-GFOWMXPYSA-N 0.000 description 3
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239000013067 intermediate product Substances 0.000 description 3
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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
- C07D401/12—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 chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
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- A61P25/20—Hypnotics; Sedatives
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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- 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
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- C07D401/14—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 three or more hetero rings
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- C07—ORGANIC CHEMISTRY
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- 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
- C07D405/12—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 chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
- C07D409/12—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 chain containing hetero atoms as chain links
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
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Rheumatology (AREA)
Ophthalmology & Optometry (AREA)
Pulmonology (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

NO923123A 1991-08-12 1992-08-11 1-acylpiperidinforbindelser, deres anvendelse for fremstilling av legemidler samt legemidler inneholdende dem NO303448B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH237491		1991-08-12

Publications (3)

Publication Number	Publication Date
NO923123D0 NO923123D0 (no)	1992-08-11
NO923123L NO923123L (no)	1993-02-15
NO303448B1 true NO303448B1 (no)	1998-07-13

Family

ID=4232283

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO923123A NO303448B1 (no)	1991-08-12	1992-08-11	1-acylpiperidinforbindelser, deres anvendelse for fremstilling av legemidler samt legemidler inneholdende dem
NO973117A NO973117D0 (no)	1991-08-12	1997-07-04	1-acylpiperidinforbindelser

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO973117A NO973117D0 (no)	1991-08-12	1997-07-04	1-acylpiperidinforbindelser

Country Status (23)

Country	Link
US (3)	US5310743A (fr)
EP (1)	EP0532456B1 (fr)
JP (1)	JP3118090B2 (fr)
KR (1)	KR100261367B1 (fr)
AT (1)	ATE120456T1 (fr)
AU (1)	AU660180B2 (fr)
CA (1)	CA2075684C (fr)
DE (1)	DE59201771D1 (fr)
DK (1)	DK0532456T3 (fr)
ES (1)	ES2070617T3 (fr)
FI (1)	FI104631B (fr)
GR (1)	GR3015954T3 (fr)
HU (1)	HU221305B1 (fr)
IL (2)	IL102769A (fr)
MX (1)	MX9204627A (fr)
MY (1)	MY110227A (fr)
NO (2)	NO303448B1 (fr)
NZ (1)	NZ243888A (fr)
PH (1)	PH29963A (fr)
RU (1)	RU2114829C1 (fr)
SA (1)	SA94140632A (fr)
TW (1)	TW204342B (fr)
ZA (1)	ZA926013B (fr)

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1992
- 1992-07-27 MY MYPI92001339A patent/MY110227A/en unknown
- 1992-07-30 PH PH44743A patent/PH29963A/en unknown
- 1992-08-01 TW TW081106123A patent/TW204342B/zh not_active IP Right Cessation
- 1992-08-04 DK DK92810594.9T patent/DK0532456T3/da active
- 1992-08-04 EP EP92810594A patent/EP0532456B1/fr not_active Expired - Lifetime
- 1992-08-04 DE DE59201771T patent/DE59201771D1/de not_active Expired - Lifetime
- 1992-08-04 ES ES92810594T patent/ES2070617T3/es not_active Expired - Lifetime
- 1992-08-04 AT AT92810594T patent/ATE120456T1/de active
- 1992-08-10 NZ NZ243888A patent/NZ243888A/en unknown
- 1992-08-10 FI FI923575A patent/FI104631B/fi not_active IP Right Cessation
- 1992-08-10 CA CA002075684A patent/CA2075684C/fr not_active Expired - Fee Related
- 1992-08-10 IL IL10276992A patent/IL102769A/en not_active IP Right Cessation
- 1992-08-10 MX MX9204627A patent/MX9204627A/es unknown
- 1992-08-10 AU AU20965/92A patent/AU660180B2/en not_active Ceased
- 1992-08-11 RU SU5052784A patent/RU2114829C1/ru active
- 1992-08-11 ZA ZA926013A patent/ZA926013B/xx unknown
- 1992-08-11 US US07/929,186 patent/US5310743A/en not_active Expired - Lifetime
- 1992-08-11 NO NO923123A patent/NO303448B1/no not_active IP Right Cessation
- 1992-08-11 KR KR1019920014407A patent/KR100261367B1/ko not_active Expired - Fee Related
- 1992-08-11 JP JP04214093A patent/JP3118090B2/ja not_active Expired - Fee Related
- 1992-08-11 HU HU9202615A patent/HU221305B1/hu not_active IP Right Cessation
1994
- 1994-03-30 SA SA94140632A patent/SA94140632A/ar unknown
- 1994-04-04 US US08/196,360 patent/US5541195A/en not_active Expired - Lifetime
1995
- 1995-04-28 GR GR950401075T patent/GR3015954T3/el unknown
- 1995-06-07 US US08/482,704 patent/US5646144A/en not_active Expired - Lifetime
1996
- 1996-06-27 IL IL11875096A patent/IL118750A0/xx unknown
1997
- 1997-07-04 NO NO973117A patent/NO973117D0/no unknown

Also Published As

Publication number	Publication date
SA94140632A (ar)	2005-12-03
KR930004297A (ko)	1993-03-22
ES2070617T3 (es)	1995-06-01
FI923575A7 (fi)	1993-02-13
PH29963A (en)	1996-09-25
MY110227A (en)	1998-03-31
NO973117D0 (no)	1997-07-04
NZ243888A (en)	1996-03-26
DK0532456T3 (da)	1995-06-12
TW204342B (fr)	1993-04-21
DE59201771D1 (de)	1995-05-04
GR3015954T3 (en)	1995-07-31
JPH07196649A (ja)	1995-08-01
US5310743A (en)	1994-05-10
US5646144A (en)	1997-07-08
ATE120456T1 (de)	1995-04-15
IL102769A0 (en)	1993-01-31
ZA926013B (en)	1993-03-31
NO923123D0 (no)	1992-08-11
CA2075684C (fr)	2003-01-07
MX9204627A (es)	1993-04-01
FI104631B (fi)	2000-03-15
US5541195A (en)	1996-07-30
HUT67088A (en)	1995-01-30
EP0532456A1 (fr)	1993-03-17
AU660180B2 (en)	1995-06-15
JP3118090B2 (ja)	2000-12-18
CA2075684A1 (fr)	1993-02-13
HU9202615D0 (en)	1992-10-28
IL102769A (en)	1999-01-26
NO973117L (no)	1993-02-15
HU221305B1 (en)	2002-09-28
AU2096592A (en)	1993-03-04
IL118750A0 (en)	1996-10-16
RU2114829C1 (ru)	1998-07-10
EP0532456B1 (fr)	1995-03-29
FI923575A0 (fi)	1992-08-10
KR100261367B1 (ko)	2000-07-01
NO923123L (no)	1993-02-15

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2012-03-26	MM1K	Lapsed by not paying the annual fees

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JP2000169449A (ja)	2000-06-20	含フッ素１，４―ジ置換ピペリジン誘導体の新規製造中間体