UA80272C2 - Process for the preparation of n-arylpiperazines (variants) and intermediate - Google Patents

Process for the preparation of n-arylpiperazines (variants) and intermediate Download PDF

Info

Publication number: UA80272C2
Authority: UA; Ukraine
Prior art keywords: formula; compound; alkyl; aroyl; group
Prior art date: 2002-03-12

Application number

UA20041008214A

Other languages

English (en)

Ukrainian (uk)

Inventor

Gregg Brian Feigelson

Joseph Zeldis

Ivo Jirkovsky

Original Assignee

Wyeth Corp

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.)

2002-03-12

Filing date

2003-10-03

Publication date

2007-09-10

2003-10-03 Application filed by Wyeth Corp filed Critical Wyeth Corp

2007-09-10 Publication of UA80272C2 publication Critical patent/UA80272C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 20
238000002360 preparation method Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims abstract description 51
230000003287 optical effect Effects 0.000 claims abstract description 3
-1 nitro, amino Chemical group 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
125000004970 halomethyl group Chemical group 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
230000003993 interaction Effects 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000003368 amide group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
125000004982 dihaloalkyl group Chemical group 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 4
125000004385 trihaloalkyl group Chemical group 0.000 claims description 4
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
125000006371 dihalo methyl group Chemical group 0.000 claims 3
125000004953 trihalomethyl group Chemical group 0.000 claims 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
238000005903 acid hydrolysis reaction Methods 0.000 claims 2
125000000172 C5-C10 aryl group Chemical group 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
230000009466 transformation Effects 0.000 claims 1
150000004885 piperazines Chemical class 0.000 abstract description 9
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 abstract description 8
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 abstract description 2
102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 abstract 1
101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
239000007787 solid Substances 0.000 description 11
239000010410 layer Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000012044 organic layer Substances 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000002585 base 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
MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
USEDMAWWQDFMFY-UHFFFAOYSA-N 4-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)C=C1 USEDMAWWQDFMFY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000027455 binding Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 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
238000000921 elemental analysis Methods 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-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
OULBFTVYYKRYRX-UHFFFAOYSA-N 5-methyl-3-pyridin-2-yloxathiazolidine 2,2-dioxide Chemical compound O=S1(=O)OC(C)CN1C1=CC=CC=N1 OULBFTVYYKRYRX-UHFFFAOYSA-N 0.000 description 1
MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 description 1
241001233887 Ania Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-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
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-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
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
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003927 aminopyridines Chemical class 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
239000011230 binding agent Substances 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
150000001721 carbon Chemical group 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 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
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000004895 liquid chromatography mass spectrometry Methods 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
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000006239 protecting group Chemical group 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
150000003839 salts Chemical group 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000013049 sediment Substances 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- 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
- C07D405/12—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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

UA20041008214A 2002-03-12 2003-10-03 Process for the preparation of n-arylpiperazines (variants) and intermediate UA80272C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US36345702P	2002-03-12	2002-03-12
PCT/US2003/007228 WO2003078396A1 (en)	2002-03-12	2003-03-10	Preparation of n1-(2’-pyridyl)-1,2-propanediamine sulfamic acid and its use in the synthesis of biologically active piperazines

Publications (1)

Publication Number	Publication Date
UA80272C2 true UA80272C2 (en)	2007-09-10

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UA20041008214A UA80272C2 (en)	2002-03-12	2003-10-03	Process for the preparation of n-arylpiperazines (variants) and intermediate

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US (1)	US6784294B2 (de)
EP (2)	EP1801103B1 (de)
JP (1)	JP4397693B2 (de)
KR (1)	KR20040091720A (de)
CN (1)	CN100341854C (de)
AR (1)	AR038932A1 (de)
AT (2)	ATE449073T1 (de)
AU (1)	AU2003220122A1 (de)
BR (1)	BR0308315A (de)
CA (1)	CA2477886A1 (de)
CY (1)	CY1106677T1 (de)
DE (2)	DE60313301T2 (de)
DK (1)	DK1483243T3 (de)
EC (1)	ECSP045291A (de)
ES (2)	ES2283762T3 (de)
IL (1)	IL163829A0 (de)
MX (1)	MXPA04008731A (de)
NO (1)	NO20044049L (de)
NZ (1)	NZ535170A (de)
PT (1)	PT1483243E (de)
RU (1)	RU2314294C2 (de)
SI (1)	SI1483243T1 (de)
TW (1)	TWI288642B (de)
UA (1)	UA80272C2 (de)
WO (1)	WO2003078396A1 (de)
ZA (1)	ZA200408213B (de)

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US20060223824A1 (en) *	2000-11-28	2006-10-05	Wyeth	Serotonergic agents
DK1408976T5 (da)	2001-07-20	2011-01-10	Psychogenics Inc	Behandling af ADHD (Attention deficit hyperactivity disorder)
US7361773B2 (en) *	2002-03-12	2008-04-22	Wyeth	Preparation of N1-(2'-pyridyl)-1,2-propanediamine sulfamic acid and its use in the synthesis of biologically active piperazines
TWI288642B (en)	2002-03-12	2007-10-21	Wyeth Corp	Preparation of N1-(2'-pyridyl)-1,2-propanediamine sulfamic acid and its use in the synthesis of biologically active piperazines
JP2005527530A (ja) *	2002-03-12	2005-09-15	ワイス	キラル１，４−二置換ピペラジン
US20070099931A1 (en) *	2004-03-19	2007-05-03	Wyeth	Pharmaceutical dosage forms and compositions
US20050209245A1 (en) *	2004-03-19	2005-09-22	Wyeth	Process for preparing N-aryl-piperazine derivatives
US20050215561A1 (en) *	2004-03-19	2005-09-29	Krishnendu Ghosh	Pharmaceutical dosage forms and compositions
BRPI0609370A2 (pt) *	2005-03-01	2010-03-30	Wyeth Corp	cloridrato de 4-ciano-n-{(2r)-2-[4-(2,3-dihidro-benzo[1,4]dioxin-5-il)-pip erazin-1-il]-propil}-n-piridin-2-il-benzamida cristalino e amorfo
CN102791691B (zh)	2010-03-12	2015-06-03	日本曹达株式会社	含有吡啶环的化合物、及卤代甲基吡啶衍生物以及四唑基肟衍生物的制造方法
EP2602248A1 (de)	2011-12-05	2013-06-12	University Of Leicester	Neue Pyrrol Verbindungen
GB201310126D0 (en) *	2013-06-06	2013-07-24	Univ Leicester	Novel pyrrole derivatives

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DE3586794T2 (de)	1984-12-21	1993-05-27	Duphar Int Res	Arzneimittel mit psychotroper wirkung.
JPH01125357A (ja)	1987-11-06	1989-05-17	Dainippon Pharmaceut Co Ltd	トリペプチドの誘導体
AU645681B2 (en)	1991-05-02	1994-01-20	John Wyeth & Brother Limited	Piperazine derivatives
WO1994024115A1 (fr)	1993-04-16	1994-10-27	Santen Pharmaceutical Co., Ltd.	Nouveau derive de piperazine
RU2118322C1 (ru) *	1993-07-05	1998-08-27	Дюфар Интернэшнл Рисерч Б.В.	2,3-дигидро-1,4-бензодиокси-5-ил-пиперазиновые производные или их соли
GB9411099D0 (en)	1994-06-03	1994-07-27	Wyeth John & Brother Ltd	Piperazine derivatives
DK0763024T3 (da) *	1994-06-03	2002-12-02	Wyeth John & Brother Ltd	Fremgangmåde og mellemprodukter til fremstilling af piperazinderivater
GB9514901D0 (en) *	1995-07-20	1995-09-20	American Home Prod	Piperazine derivatives
WO1997037655A1 (en)	1996-04-10	1997-10-16	Merck & Co., Inc.	αvβ3 ANTAGONISTS
TWI288642B (en)	2002-03-12	2007-10-21	Wyeth Corp	Preparation of N1-(2'-pyridyl)-1,2-propanediamine sulfamic acid and its use in the synthesis of biologically active piperazines
US6713626B2 (en) *	2002-03-12	2004-03-30	Wyeth	Process for synthesizing N-aryl piperazines with chiral N′-1-[benzoyl(2-pyridyl)amino]-2-propane substitution

2003
- 2003-03-10 TW TW092105099A patent/TWI288642B/zh not_active IP Right Cessation
- 2003-03-10 AT AT07007755T patent/ATE449073T1/de not_active IP Right Cessation
- 2003-03-10 IL IL16382903A patent/IL163829A0/xx unknown
- 2003-03-10 WO PCT/US2003/007228 patent/WO2003078396A1/en not_active Ceased
- 2003-03-10 DK DK03716415T patent/DK1483243T3/da active
- 2003-03-10 BR BR0308315-2A patent/BR0308315A/pt not_active IP Right Cessation
- 2003-03-10 JP JP2003576402A patent/JP4397693B2/ja not_active Expired - Fee Related
- 2003-03-10 EP EP07007755A patent/EP1801103B1/de not_active Expired - Lifetime
- 2003-03-10 DE DE60313301T patent/DE60313301T2/de not_active Expired - Lifetime
- 2003-03-10 DE DE60330199T patent/DE60330199D1/de not_active Expired - Lifetime
- 2003-03-10 US US10/385,337 patent/US6784294B2/en not_active Expired - Fee Related
- 2003-03-10 CN CNB038058421A patent/CN100341854C/zh not_active Expired - Fee Related
- 2003-03-10 CA CA002477886A patent/CA2477886A1/en not_active Abandoned
- 2003-03-10 RU RU2004130314/04A patent/RU2314294C2/ru not_active IP Right Cessation
- 2003-03-10 ES ES03716415T patent/ES2283762T3/es not_active Expired - Lifetime
- 2003-03-10 PT PT03716415T patent/PT1483243E/pt unknown
- 2003-03-10 KR KR10-2004-7014252A patent/KR20040091720A/ko not_active Abandoned
- 2003-03-10 AT AT03716415T patent/ATE360002T1/de not_active IP Right Cessation
- 2003-03-10 MX MXPA04008731A patent/MXPA04008731A/es active IP Right Grant
- 2003-03-10 NZ NZ535170A patent/NZ535170A/xx unknown
- 2003-03-10 SI SI200330817T patent/SI1483243T1/sl unknown
- 2003-03-10 AU AU2003220122A patent/AU2003220122A1/en not_active Abandoned
- 2003-03-10 EP EP03716415A patent/EP1483243B1/de not_active Expired - Lifetime
- 2003-03-10 ES ES07007755T patent/ES2334836T3/es not_active Expired - Lifetime
- 2003-03-11 AR ARP030100833A patent/AR038932A1/es unknown
- 2003-10-03 UA UA20041008214A patent/UA80272C2/uk unknown
2004
- 2004-09-10 EC EC2004005291A patent/ECSP045291A/es unknown
- 2004-09-24 NO NO20044049A patent/NO20044049L/no not_active Application Discontinuation
- 2004-10-11 ZA ZA200408213A patent/ZA200408213B/en unknown
2007
- 2007-06-26 CY CY20071100843T patent/CY1106677T1/el unknown

Also Published As

Publication number	Publication date
JP4397693B2 (ja)	2010-01-13
JP2005526088A (ja)	2005-09-02
DE60313301T2 (de)	2007-12-27
ES2334836T3 (es)	2010-03-16
US6784294B2 (en)	2004-08-31
DE60313301D1 (de)	2007-05-31
IL163829A0 (en)	2005-12-18
BR0308315A (pt)	2004-12-28
ZA200408213B (en)	2007-03-28
MXPA04008731A (es)	2004-12-06
ES2283762T3 (es)	2007-11-01
NO20044049L (no)	2004-09-24
ATE449073T1 (de)	2009-12-15
EP1801103A1 (de)	2007-06-27
CN1642916A (zh)	2005-07-20
TWI288642B (en)	2007-10-21
CN100341854C (zh)	2007-10-10
DK1483243T3 (da)	2007-08-06
RU2004130314A (ru)	2005-04-10
EP1801103B1 (de)	2009-11-18
ECSP045291A (es)	2004-10-26
WO2003078396A8 (en)	2004-01-29
DE60330199D1 (de)	2009-12-31
HK1068618A1 (en)	2005-04-29
EP1483243B1 (de)	2007-04-18
PT1483243E (pt)	2007-06-27
KR20040091720A (ko)	2004-10-28
AU2003220122A1 (en)	2003-09-29
CY1106677T1 (el)	2012-05-23
ATE360002T1 (de)	2007-05-15
TW200303751A (en)	2003-09-16
AR038932A1 (es)	2005-02-02
WO2003078396A1 (en)	2003-09-25
NZ535170A (en)	2006-03-31
SI1483243T1 (sl)	2007-08-31
EP1483243A1 (de)	2004-12-08
RU2314294C2 (ru)	2008-01-10
CA2477886A1 (en)	2003-09-25
US20030204087A1 (en)	2003-10-30

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