IL109802A - Pharmaceutical preparations containing 2 methoxybenzylamines are converted to position N for the treatment of vomiting - Google Patents

Pharmaceutical preparations containing 2 methoxybenzylamines are converted to position N for the treatment of vomiting

Info

Publication number: IL109802A
Authority: IL; Israel
Prior art keywords: alkyl; phenyl; compound; formula; diphenylmethyl
Prior art date: 1993-06-04

Application number

IL10980294A

Other languages

English (en)

Hebrew (he)

Other versions

IL109802A0 (en

Original Assignee

Pfizer

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.)

1993-06-04

Filing date

1994-05-26

Publication date

2002-04-21

1994-05-26 Application filed by Pfizer filed Critical Pfizer

1994-08-26 Publication of IL109802A0 publication Critical patent/IL109802A0/xx

2002-04-21 Publication of IL109802A publication Critical patent/IL109802A/en

Links

206010047700 Vomiting Diseases 0.000 title claims abstract description 47
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
PXJACNDVRNAFHD-UHFFFAOYSA-N (2-methoxyphenyl)methanamine Chemical class COC1=CC=CC=C1CN PXJACNDVRNAFHD-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 175
-1 5-tert-butyl-2- methoxyphenyl Chemical group 0.000 claims description 87
150000003839 salts Chemical class 0.000 claims description 35
239000003814 drug Substances 0.000 claims description 26
JASMWYNKLTULAN-UHFFFAOYSA-N octan-3-amine Chemical compound CCCCCC(N)CC JASMWYNKLTULAN-UHFFFAOYSA-N 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 10
IWNUVCPVRJASIF-CONSDPRKSA-N (2s,3s)-2-benzhydryl-n-(2-methoxy-5-propan-2-ylphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C(C)C)C=C1N[C@@H]1[C@@](C(C=2C=CC=CC=2)C=2C=CC=CC=2)(C)N2CCC1CC2 IWNUVCPVRJASIF-CONSDPRKSA-N 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
239000003890 substance P antagonist Substances 0.000 claims description 2
ZXKQLZMZYWXUJC-CDZUIXILSA-N (2s,3s)-2-benzhydryl-n-(5-tert-butyl-2-methoxyphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C(C)(C)C)C=C1N[C@@H]1[C@@](C(C=2C=CC=CC=2)C=2C=CC=CC=2)(C)N2CCC1CC2 ZXKQLZMZYWXUJC-CDZUIXILSA-N 0.000 claims 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
241000124008 Mammalia Species 0.000 abstract description 36
150000003053 piperidines Chemical class 0.000 abstract 1
150000008584 quinuclidines Chemical class 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 description 241
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 128
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 80
229910052739 hydrogen Inorganic materials 0.000 description 73
239000001257 hydrogen Substances 0.000 description 73
125000003545 alkoxy group Chemical group 0.000 description 70
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 64
125000001153 fluoro group Chemical group F* 0.000 description 59
125000001424 substituent group Chemical group 0.000 description 58
125000004432 carbon atom Chemical group C* 0.000 description 52
125000003282 alkyl amino group Chemical group 0.000 description 43
125000005843 halogen group Chemical group 0.000 description 42
229910052799 carbon Inorganic materials 0.000 description 40
150000002431 hydrogen Chemical class 0.000 description 38
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 37
238000000034 method Methods 0.000 description 35
229910052757 nitrogen Inorganic materials 0.000 description 35
125000003118 aryl group Chemical group 0.000 description 34
125000001544 thienyl group Chemical group 0.000 description 34
125000001624 naphthyl group Chemical group 0.000 description 29
125000004076 pyridyl group Chemical group 0.000 description 29
125000002541 furyl group Chemical group 0.000 description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 description 27
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 26
229910052760 oxygen Inorganic materials 0.000 description 22
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 21
239000001301 oxygen Substances 0.000 description 21
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 20
125000001072 heteroaryl group Chemical group 0.000 description 20
125000000335 thiazolyl group Chemical group 0.000 description 20
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 19
125000002971 oxazolyl group Chemical group 0.000 description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 19
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 18
229910052717 sulfur Chemical group 0.000 description 18
239000011593 sulfur Chemical group 0.000 description 18
239000011203 carbon fibre reinforced carbon Substances 0.000 description 17
150000001721 carbon Chemical group 0.000 description 16
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
125000005493 quinolyl group Chemical group 0.000 description 16
125000003831 tetrazolyl group Chemical group 0.000 description 16
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 15
229940124597 therapeutic agent Drugs 0.000 description 15
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 14
125000001786 isothiazolyl group Chemical group 0.000 description 14
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
125000001425 triazolyl group Chemical group 0.000 description 13
125000000842 isoxazolyl group Chemical group 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
102000002002 Neurokinin-1 Receptors Human genes 0.000 description 9
108010040718 Neurokinin-1 Receptors Proteins 0.000 description 9
239000002253 acid Substances 0.000 description 9
125000004356 hydroxy functional group Chemical group O* 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
239000000243 solution Substances 0.000 description 9
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 8
239000004305 biphenyl Chemical group 0.000 description 8
235000010290 biphenyl Nutrition 0.000 description 8
239000007858 starting material Substances 0.000 description 8
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
125000002883 imidazolyl group Chemical group 0.000 description 7
239000002464 receptor antagonist Substances 0.000 description 7
229940044551 receptor antagonist Drugs 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 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 description 6
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
102100024304 Protachykinin-1 Human genes 0.000 description 6
101800003906 Substance P Proteins 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 6
125000002837 carbocyclic group Chemical group 0.000 description 6
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
125000004952 trihaloalkoxy group Chemical group 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
230000000694 effects Effects 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 5
125000001041 indolyl group Chemical group 0.000 description 5
UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 5
YSEQNZOXHCKLOG-UHFFFAOYSA-N 2-methyl-octanoic acid Chemical compound CCCCCCC(C)C(O)=O YSEQNZOXHCKLOG-UHFFFAOYSA-N 0.000 description 4
206010015866 Extravasation Diseases 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241000282339 Mustela Species 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
239000007983 Tris buffer Substances 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
125000004414 alkyl thio group Chemical group 0.000 description 4
150000001413 amino acids Chemical class 0.000 description 4
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 4
125000002619 bicyclic group Chemical group 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
230000036251 extravasation Effects 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Chemical group 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
125000002950 monocyclic group Chemical group 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
125000004043 oxo group Chemical group O=* 0.000 description 4
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
125000003226 pyrazolyl group Chemical group 0.000 description 4
125000000168 pyrrolyl group Chemical group 0.000 description 4
125000003107 substituted aryl group Chemical group 0.000 description 4
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000283690 Bos taurus Species 0.000 description 3
229910014033 C-OH Inorganic materials 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
229910014570 C—OH Inorganic materials 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
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 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
230000027455 binding Effects 0.000 description 3
235000017663 capsaicin Nutrition 0.000 description 3
229960002504 capsaicin Drugs 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
125000004663 dialkyl amino group Chemical group 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000000975 dye Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
150000002466 imines Chemical class 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
239000003446 ligand Substances 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
125000005646 oximino group Chemical group 0.000 description 3
125000000714 pyrimidinyl group Chemical group 0.000 description 3
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 3
238000006268 reductive amination reaction Methods 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000001113 thiadiazolyl group Chemical group 0.000 description 3
DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 description 3
CAWVBTFOZJKLOD-LAUBAEHRSA-N (2s,3s)-2-phenyl-3-[[2-propan-2-yloxy-5-(trifluoromethoxy)phenyl]methyl]piperidin-1-amine Chemical compound CC(C)OC1=CC=C(OC(F)(F)F)C=C1C[C@H]1[C@@H](C=2C=CC=CC=2)N(N)CCC1 CAWVBTFOZJKLOD-LAUBAEHRSA-N 0.000 description 2
DTQNEFOKTXXQKV-HKUYNNGSSA-N (2s,3s)-n-[(2-methoxyphenyl)methyl]-2-phenylpiperidin-3-amine Chemical compound COC1=CC=CC=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 DTQNEFOKTXXQKV-HKUYNNGSSA-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 2
XQDSIGDVDWFZPP-UHFFFAOYSA-N 2-phenylpiperidin-1-amine Chemical compound NN1CCCCC1C1=CC=CC=C1 XQDSIGDVDWFZPP-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
125000005236 alkanoylamino group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
125000002618 bicyclic heterocycle group Chemical group 0.000 description 2
239000001045 blue dye Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
229910000085 borane Inorganic materials 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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RLQOSRPUKJCKQO-JDXGNMNLSA-N n-[5-[(2s,3s)-3-[(2-methoxyphenyl)methylamino]-2-phenylpiperidin-1-yl]pentyl]benzamide Chemical compound COC1=CC=CC=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)N(CCCCCNC(=O)C=2C=CC=CC=2)CCC1 RLQOSRPUKJCKQO-JDXGNMNLSA-N 0.000 description 1
WUBHPPKTNIKCBX-UHFFFAOYSA-N n-[[2-methoxy-5-(trifluoromethoxy)phenyl]methyl]-3-(2h-pyridin-1-yl)bicyclo[2.2.1]heptan-2-amine Chemical compound COC1=CC=C(OC(F)(F)F)C=C1CNC1C(N2C=CC=CC2)C2CCC1C2 WUBHPPKTNIKCBX-UHFFFAOYSA-N 0.000 description 1
230000008693 nausea Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000000014 opioid analgesic Substances 0.000 description 1
229940005483 opioid analgesics Drugs 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000008203 oral pharmaceutical composition Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000012026 peptide coupling reagents‎ Substances 0.000 description 1
206010034674 peritonitis Diseases 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
229960000624 procarbazine Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000006340 racemization Effects 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229960001790 sodium citrate Drugs 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
150000003413 spiro compounds Chemical class 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
108060008037 tachykinin Proteins 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108700012359 toxins Proteins 0.000 description 1
210000000626 ureter Anatomy 0.000 description 1
208000027491 vestibular disease Diseases 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
208000009935 visceral pain Diseases 0.000 description 1
230000008673 vomiting Effects 0.000 description 1

Classifications

- 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
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- 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
- 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
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Chemistry (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Hydrogenated Pyridines (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pyrrole Compounds (AREA)
Chemical Or Physical Treatment Of Fibers (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)

IL10980294A 1993-06-04 1994-05-26 Pharmaceutical preparations containing 2 methoxybenzylamines are converted to position N for the treatment of vomiting IL109802A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/072,629 US5393762A (en)	1993-06-04	1993-06-04	Pharmaceutical agents for treatment of emesis

Publications (2)

Publication Number	Publication Date
IL109802A0 IL109802A0 (en)	1994-08-26
IL109802A true IL109802A (en)	2002-04-21

Family

ID=22108825

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10980294A IL109802A (en)	1993-06-04	1994-05-26	Pharmaceutical preparations containing 2 methoxybenzylamines are converted to position N for the treatment of vomiting

Country Status (19)

Country	Link
US (1)	US5393762A (de)
EP (1)	EP0627221B1 (de)
JP (1)	JP2671972B2 (de)
KR (1)	KR100190729B1 (de)
CN (1)	CN1100535C (de)
AT (1)	ATE209490T1 (de)
AU (1)	AU666077B2 (de)
CA (1)	CA2124990C (de)
DE (1)	DE69429208T2 (de)
DK (1)	DK0627221T3 (de)
ES (1)	ES2164088T3 (de)
HU (1)	HU222243B1 (de)
IL (1)	IL109802A (de)
MY (1)	MY115310A (de)
NZ (1)	NZ260674A (de)
PT (1)	PT627221E (de)
RU (1)	RU2135179C1 (de)
TW (1)	TW318791B (de)
ZA (1)	ZA943896B (de)

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US5576317A (en) *	1994-12-09	1996-11-19	Pfizer Inc.	NK-1 receptor antagonists and 5HT3 receptor antagonists for the treatment of emesis
KR19980703354A (ko) *	1995-03-27	1998-10-15	나카토미히로타카	피페리딘 유도체
TW340842B (en)	1995-08-24	1998-09-21	Pfizer	Substituted benzylaminopiperidine compounds
TW458774B (en) *	1995-10-20	2001-10-11	Pfizer	Antiemetic pharmaceutical compositions
US6329396B1 (en)	1996-06-10	2001-12-11	Pfizer Inc.	Substituted benzylaminopiperidine compounds
GB9708484D0 (en)	1997-04-25	1997-06-18	Merck Sharp & Dohme	Therapeutic agents
US6214846B1 (en) *	1997-06-27	2001-04-10	Merck Sharp & Dohme Limited	Substituted 3-(benzylamino)piperidine derivatives and their use as therapeutic agents
AU1409100A (en) *	1998-11-27	2000-06-19	Takeda Chemical Industries Ltd.	Drugs
NZ501211A (en) *	1999-01-29	2001-10-26	Pfizer Prod Inc	Pharmaceutical composition comprising macrolide antibiotic like erythromycin and a Substance P antagonist, and method for treating cancer, bacterial and protozoal infection in non-humans
US6387925B1 (en) *	1999-06-01	2002-05-14	Pfizer Inc.	Polymorphs of a crystalline azo-bicyclo (2.2.2) oct-3-yl amine citrate and their pharmaceutical compositions
US6255320B1 (en) *	1999-06-01	2001-07-03	Pfizer Inc.	Polymorphs of a crystalline azo-bicyclo (2,2,2) octan-3-amine citrate and their pharmaceutical compositions
US6262067B1 (en) *	1999-06-22	2001-07-17	Pfizer Inc.	Polymorphs of a crystalline azo-bicyclo 2,2,2 OCT-3-yl amine dihydrochloride and their pharmaceutical compositions
IL142810A0 (en) *	2000-05-03	2002-03-10	Pfizer Prod Inc	Pharmaceutical uses for fluoroalkoxybenzylamino derivatives of nitrogen containing heterocycles
RU2197961C2 (ru) *	2000-07-17	2003-02-10	Центр по разработке эластомеров Казанского государственного технологического университета	Средство для профилактики и купирования тошноты и рвоты
RU2183118C1 (ru) *	2001-07-12	2002-06-10	Государственный научный центр РФ Институт медико-биологических проблем РАН	Способ профилактики вестибуловегетативных расстройств у человека в условиях воздействий, вызывающих укачивание
KR20040029375A (ko) *	2001-07-20	2004-04-06	화이자 프로덕츠 인코포레이티드	개, 고양이 및 말에서 결함있는 행태를 변화시키기 위한ｎｋ-1 수용체 길항제의 용도
KR100880391B1 (ko) *	2004-01-30	2009-01-30	화이자 프로덕츠 인크.	마취 회복 개선용 ｎｋ-1 수용체 길항제
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1993
- 1993-06-04 US US08/072,629 patent/US5393762A/en not_active Expired - Lifetime
1994
- 1994-04-12 TW TW083103232A patent/TW318791B/zh active
- 1994-05-16 PT PT94303467T patent/PT627221E/pt unknown
- 1994-05-16 DE DE69429208T patent/DE69429208T2/de not_active Expired - Fee Related
- 1994-05-16 AT AT94303467T patent/ATE209490T1/de not_active IP Right Cessation
- 1994-05-16 EP EP94303467A patent/EP0627221B1/de not_active Expired - Lifetime
- 1994-05-16 ES ES94303467T patent/ES2164088T3/es not_active Expired - Lifetime
- 1994-05-16 DK DK94303467T patent/DK0627221T3/da active
- 1994-05-26 IL IL10980294A patent/IL109802A/en not_active IP Right Cessation
- 1994-06-02 JP JP6121042A patent/JP2671972B2/ja not_active Expired - Fee Related
- 1994-06-02 CA CA002124990A patent/CA2124990C/en not_active Expired - Fee Related
- 1994-06-02 MY MYPI94001422A patent/MY115310A/en unknown
- 1994-06-03 HU HU9401676A patent/HU222243B1/hu not_active IP Right Cessation
- 1994-06-03 KR KR1019940012527A patent/KR100190729B1/ko not_active Expired - Fee Related
- 1994-06-03 ZA ZA943896A patent/ZA943896B/xx unknown
- 1994-06-03 NZ NZ260674A patent/NZ260674A/en not_active IP Right Cessation
- 1994-06-03 CN CN94106917A patent/CN1100535C/zh not_active Expired - Fee Related
- 1994-06-03 RU RU94020410A patent/RU2135179C1/ru not_active IP Right Cessation
- 1994-06-03 AU AU64521/94A patent/AU666077B2/en not_active Ceased

Also Published As

Publication number	Publication date
ZA943896B (en)	1995-12-04
EP0627221B1 (de)	2001-11-28
EP0627221A2 (de)	1994-12-07
KR100190729B1 (ko)	1999-06-01
CA2124990C (en)	1999-04-20
HU9401676D0 (en)	1994-09-28
HUT71550A (en)	1995-12-28
DK0627221T3 (da)	2002-02-11
NZ260674A (en)	2000-07-28
JP2671972B2 (ja)	1997-11-05
US5393762A (en)	1995-02-28
AU666077B2 (en)	1996-01-25
PT627221E (pt)	2002-04-29
IL109802A0 (en)	1994-08-26
TW318791B (de)	1997-11-01
DE69429208T2 (de)	2002-05-23
AU6452194A (en)	1994-12-15
ATE209490T1 (de)	2001-12-15
CN1100535C (zh)	2003-02-05
MY115310A (en)	2003-05-31
RU2135179C1 (ru)	1999-08-27
KR950000144A (ko)	1995-01-03
EP0627221A3 (de)	1995-08-02
DE69429208D1 (de)	2002-01-10
HU222243B1 (hu)	2003-05-28
ES2164088T3 (es)	2002-02-16
JPH0753362A (ja)	1995-02-28
CN1121806A (zh)	1996-05-08
RU94020410A (ru)	1996-05-10

Legal Events

Date	Code	Title
2002-09-12	FF	Patent granted
2002-11-10	KB	Patent renewed
2004-06-20	KB	Patent renewed
2008-08-10	KB	Patent renewed
2013-02-03	MM9K	Patent not in force due to non-payment of renewal fees

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US20010036943A1 (en)	2001-11-01	Pharmaceutical composition for treatment of acute, chronic pain and/or neuropathic pain and migraines
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KR19980080824A (ko)	1998-11-25	지연성 구토 치료를 위한 ｎｋ-1 수용체 길항제
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