NO781450L - Fremgangsmaate for fremstilling av nye n-(1-(3-benzoylpropyl)-4-piperidyl)-sulfonsyreamider - Google Patents

Fremgangsmaate for fremstilling av nye n-(1-(3-benzoylpropyl)-4-piperidyl)-sulfonsyreamider

Info

Publication number: NO781450L
Authority: NO; Norway
Prior art keywords: formula; acid; piperidyl; compound; general formula
Prior art date: 1977-04-26

Application number

NO781450A

Other languages

English (en)

Norwegian (no)

Inventor

Adolf Langbein

Karl-Heinz Weber

Karin Boeke

Original Assignee

Boehringer Sohn Ingelheim

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.)

1977-04-26

Filing date

1978-04-25

Publication date

1978-10-27

1978-04-25 Application filed by Boehringer Sohn Ingelheim filed Critical Boehringer Sohn Ingelheim

1978-10-27 Publication of NO781450L publication Critical patent/NO781450L/no

Links

238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 11
-1 N-[1-(3-(4-fluorobenzoyl)propyl)-4-piperidyl]-methanesulfonamide Chemical compound 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 3
TWILTNTVUCNZRL-UHFFFAOYSA-N C=1C=CC=CC=1C(=O)CCCN1CCC(NS(=O)=O)CC1 Chemical class C=1C=CC=CC=1C(=O)CCCN1CCC(NS(=O)=O)CC1 TWILTNTVUCNZRL-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
RLKSQLJFGCDUOX-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-4-chlorobutan-1-one Chemical compound CC(C)(C)C1=CC=C(C(=O)CCCCl)C=C1 RLKSQLJFGCDUOX-UHFFFAOYSA-N 0.000 claims 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
239000012467 final product Substances 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
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 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 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
238000001816 cooling Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000000047 product Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229940025084 amphetamine Drugs 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
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 2
229960004046 apomorphine Drugs 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 2
230000002903 catalepsic effect Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
125000001072 heteroaryl group Chemical group 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 2
WDUGZBMCSAVLRP-UHFFFAOYSA-N n-piperidin-1-ylmethanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NN1CCCCC1 WDUGZBMCSAVLRP-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
LSIOKIFIROCRRF-UHFFFAOYSA-N (1-benzylpiperidin-4-yl)methanesulfonamide;hydrochloride Chemical compound Cl.C1CC(CS(=O)(=O)N)CCN1CC1=CC=CC=C1 LSIOKIFIROCRRF-UHFFFAOYSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-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
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-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
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-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
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
230000000561 anti-psychotic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000009227 behaviour therapy Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000015572 biosynthetic process 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
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
239000012442 inert solvent Substances 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
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
XFNZLWPRVFVAEW-UHFFFAOYSA-N n-piperidin-1-ylmethanesulfonamide Chemical compound CS(=O)(=O)NN1CCCCC1 XFNZLWPRVFVAEW-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
235000011007 phosphoric acid Nutrition 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
239000011541 reaction mixture Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

NO781450A 1977-04-26 1978-04-25 Fremgangsmaate for fremstilling av nye n-(1-(3-benzoylpropyl)-4-piperidyl)-sulfonsyreamider NO781450L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772718405 DE2718405A1 (de)	1977-04-26	1977-04-26	Neue n- eckige klammer auf 1-(3-benzoylpropyl)-4-piperidyl eckige klammer zu -sulfonsaeureamide und verfahren zu deren herstellung

Publications (1)

Publication Number	Publication Date
NO781450L true NO781450L (no)	1978-10-27

Family

ID=6007245

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO781450A NO781450L (no)	1977-04-26	1978-04-25	Fremgangsmaate for fremstilling av nye n-(1-(3-benzoylpropyl)-4-piperidyl)-sulfonsyreamider

Country Status (23)

Country	Link
US (1)	US4145427A (fr)
JP (1)	JPS53132579A (fr)
AT (1)	AT364823B (fr)
AU (1)	AU519705B2 (fr)
BE (1)	BE866351A (fr)
CA (1)	CA1097648A (fr)
DE (1)	DE2718405A1 (fr)
DK (1)	DK179278A (fr)
ES (2)	ES469108A1 (fr)
FI (1)	FI781177A7 (fr)
FR (1)	FR2388795A1 (fr)
GB (1)	GB1563989A (fr)
GR (1)	GR64514B (fr)
IL (1)	IL54574A (fr)
IT (1)	IT1104811B (fr)
LU (1)	LU79515A1 (fr)
NL (1)	NL7804388A (fr)
NO (1)	NO781450L (fr)
NZ (1)	NZ187060A (fr)
PH (1)	PH15717A (fr)
PT (1)	PT67949B (fr)
SE (1)	SE7804743L (fr)
ZA (1)	ZA782340B (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4246268A (en) *	1979-02-09	1981-01-20	Richardson-Merrell Inc.	Neuroleptic-4-(naphthylmethyl)piperidine derivatives
NZ193654A (en)	1979-05-16	1984-08-24	Wuelfing Johann A	Naphthalene sulphonamido-alkyl-piperidines,pyrrolidines or piperazines and pharmaceutical compositions
US4443462A (en) *	1979-08-06	1984-04-17	Merrell Dow Pharmaceuticals Inc.	Antipsychotic 4-(naphthalenyloxy)piperidine derivatives
IE49998B1 (en) *	1979-08-06	1986-01-22	Merrell Dow Pharma	4-(naphthalenyloxy)piperidine derivatives
US5210090A (en) *	1989-09-05	1993-05-11	G. D. Searle & Co.	Substituted N-benzylpiperidine amides and cardiac regulatory compositions thereof
AU2001288972A1 (en)	2000-09-11	2002-03-26	Sepracor, Inc.	Antipsychotic sulfonamide-heterocycles, and methods of use thereof
SI1594840T1 (sl) *	2003-02-17	2006-12-31	Hoffmann La Roche	Derivati piperidin-benzensulfonamida
TW200630337A (en)	2004-10-14	2006-09-01	Euro Celtique Sa	Piperidinyl compounds and the use thereof
US8247442B2 (en) *	2006-03-29	2012-08-21	Purdue Pharma L.P.	Benzenesulfonamide compounds and their use
WO2007118853A1 (fr) *	2006-04-13	2007-10-25	Euro-Celtique S.A.	Benzènesulfonamides et leur emploi en tant qu'agents bloquants des canaux calcium
TW200812963A (en) *	2006-04-13	2008-03-16	Euro Celtique Sa	Benzenesulfonamide compounds and the use thereof
MX2008014450A (es) *	2006-05-18	2009-03-09	Mannkind Corp	Inhibidores de cinasa intracelular.
US8399486B2 (en) *	2007-04-09	2013-03-19	Purdue Pharma L.P.	Benzenesulfonyl compounds and the use thereof
EP2532643A1 (fr)	2007-06-08	2012-12-12	MannKind Corporation	Inhibiteurs IRE-1A
US8765736B2 (en) *	2007-09-28	2014-07-01	Purdue Pharma L.P.	Benzenesulfonamide compounds and the use thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB948071A (en) *	1959-05-01	1964-01-29	May & Baker Ltd	New heterocyclic compounds
US3932649A (en) *	1972-08-12	1976-01-13	Pfizer Inc.	2 And 3-substituted-4-(heterocyclic-amino-sulfonyl)benzene sulfonamides as cerebral vasodilators
US3932636A (en) *	1972-08-12	1976-01-13	Pfizer Inc.	2 And 3-substituted-4-(heterocyclic-amino-sulfonyl)benzene sulfonamides as cerebral vasodilators
US3932647A (en) *	1973-08-09	1976-01-13	Pfizer Inc.	Cyclic N-substituted derivatives of 1,4-benzene disulphonamide
GB1482099A (en) *	1974-12-11	1977-08-03	Wyeth John & Brother Ltd	Sulphonamido derivatives

1977
- 1977-04-26 DE DE19772718405 patent/DE2718405A1/de not_active Withdrawn
1978
- 1978-04-13 PH PH21001A patent/PH15717A/en unknown
- 1978-04-14 US US05/896,575 patent/US4145427A/en not_active Expired - Lifetime
- 1978-04-14 AT AT0261578A patent/AT364823B/de not_active IP Right Cessation
- 1978-04-18 FI FI781177A patent/FI781177A7/fi not_active Application Discontinuation
- 1978-04-20 GR GR56039A patent/GR64514B/el unknown
- 1978-04-24 PT PT67949A patent/PT67949B/pt unknown
- 1978-04-24 IT IT49045/78A patent/IT1104811B/it active
- 1978-04-24 JP JP4866778A patent/JPS53132579A/ja active Pending
- 1978-04-24 NZ NZ187060A patent/NZ187060A/xx unknown
- 1978-04-24 LU LU79515A patent/LU79515A1/de unknown
- 1978-04-25 ZA ZA00782340A patent/ZA782340B/xx unknown
- 1978-04-25 NL NL7804388A patent/NL7804388A/xx not_active Application Discontinuation
- 1978-04-25 NO NO781450A patent/NO781450L/no unknown
- 1978-04-25 CA CA301,885A patent/CA1097648A/fr not_active Expired
- 1978-04-25 ES ES469108A patent/ES469108A1/es not_active Expired
- 1978-04-25 BE BE187089A patent/BE866351A/fr unknown
- 1978-04-25 DK DK179278A patent/DK179278A/da not_active Application Discontinuation
- 1978-04-25 GB GB16308/78A patent/GB1563989A/en not_active Expired
- 1978-04-25 IL IL54574A patent/IL54574A/xx unknown
- 1978-04-25 SE SE7804743A patent/SE7804743L/xx unknown
- 1978-04-26 FR FR7812366A patent/FR2388795A1/fr not_active Withdrawn
- 1978-04-26 AU AU35453/78A patent/AU519705B2/en not_active Expired
- 1978-08-08 ES ES472448A patent/ES472448A1/es not_active Expired

Also Published As

Publication number	Publication date
ATA261578A (de)	1981-04-15
FR2388795A1 (fr)	1978-11-24
AU519705B2 (en)	1981-12-17
GR64514B (en)	1980-04-09
JPS53132579A (en)	1978-11-18
DK179278A (da)	1978-10-27
IL54574A (en)	1981-09-13
NL7804388A (nl)	1978-10-30
ES472448A1 (es)	1979-05-01
IT1104811B (it)	1985-10-28
AU3545378A (en)	1979-11-01
ES469108A1 (es)	1978-11-16
NZ187060A (en)	1980-11-28
DE2718405A1 (de)	1978-11-02
US4145427A (en)	1979-03-20
BE866351A (fr)	1978-10-25
IL54574A0 (en)	1978-07-31
SE7804743L (sv)	1978-10-27
ZA782340B (en)	1979-12-27
PT67949A (de)	1978-05-01
GB1563989A (en)	1980-04-02
FI781177A7 (fi)	1978-10-27
LU79515A1 (de)	1979-05-25
PT67949B (de)	1980-06-16
AT364823B (de)	1981-11-25
IT7849045A0 (it)	1978-04-24
CA1097648A (fr)	1981-03-17
PH15717A (en)	1983-03-18

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CN101896459B (zh)	2013-07-24	驱肠虫药及其用途
US5464788A (en)	1995-11-07	Tocolytic oxytocin receptor antagonists
NO313189B1 (no)	2002-08-26	Aryloksyarylsulfonylaminohydroksy-aminosyrederivater og farmasöytisk blanding
JP2002504483A (ja)	2002-02-12	ヒスタミンｈ３受容体リガンド
NO167947B (no)	1991-09-16	Lagringsanordning for baand- eller plate-registreringsmedier
DE69805473T2 (de)	2003-01-16	Arylsulfonylaminohydroxamsäurederivate
NO884008L (no)	1989-03-10	Fremgangsmaate for fremstilling av 3,7-diazabicyclo(3,3,1)nonanforbindelser.
NO823587L (no)	1983-04-29	Laktoner.
NO135751B (fr)	1977-02-14
NO136713B (fr)	1977-07-18
BR112020013794A2 (pt)	2020-12-01	processo para a preparação de crisaborola de fórmula (i), compostos, uso de um composto de fórmula (iv), (iii) ou (ii), processo para a preparação de crisaborola altamente pura e sal
EP0078241A2 (fr)	1983-05-04	Furans
NO127746B (fr)	1973-08-13
EP0073645B1 (fr)	1986-11-12	Dérivés d'esters d'acides 2-cyclamino-2-(1,2-benzisoxazol-3-yl)-acétiques, procédé pour leur préparation et composition les contenant
KR19990082986A (ko)	1999-11-25	장애 설폰아미드를 알킬화시키는 방법
NO843203L (no)	1985-02-12	Fremgangsmaate for fremstilling av indolderivater
Lednicer et al.	1968	Synthesis and Antifertility Activity of 4-and5-(ι-Arylalkyl) oxazolidinethiones
NO139050B (no)	1978-09-18	Analogifremgangsmaate for fremstilling av terapeutisk aktive nororipavin- og tebainderivater
IL24192A (en)	1969-03-27	1-phenylsulfonyl-2-benzimidazolinones and 1-phenylsulfonyl-2-benzimidazolinethiones and process for their preparation
Garbrecht et al.	1950	N-(β-Chloroethyl)-2, 3-dihydro-1-benz [de] isoquinoline Hydrochloride
DE3816634A1 (de)	1988-11-24	Cyclobuten-3,4-dion-zwischenverbindungen, verfahren zu ihrer herstellung und ihre verwendung
US3786068A (en)	1974-01-15	Intermediate in the total synthesis of elenolic acid
KR810000690B1 (ko)	1981-06-22	N-[1-(3-벤조일프로필)-4-피페리딜]-설폰산 아미드의 제조방법