SK15552003A3 - Oxadiazolové a tiadiazolové deriváty pyrolidínu, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Oxadiazolové a tiadiazolové deriváty pyrolidínu, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK15552003A3
Authority: SK; Slovakia
Prior art keywords: biphenyl; oxadiazol; ylcarbonyl; pyrrolidinone; methyloxime
Prior art date: 2001-06-18

Application number

SK1555-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Matthias Schwarz

Anna Quattropani

Patrick Page

Russell J. Thomas

Vincent Pomel

Original Assignee

Applied Research Systems Ars Holding N. V.

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.)

2001-06-18

Filing date

2002-06-14

Publication date

2004-05-04

2002-06-14 Application filed by Applied Research Systems Ars Holding N. V. filed Critical Applied Research Systems Ars Holding N. V.

2004-05-04 Publication of SK15552003A3 publication Critical patent/SK15552003A3/sk

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-1 Pyrrolidine oxadiazole- and thiadiazole oxime Chemical class 0.000 title claims abstract description 294
229940122828 Oxytocin receptor antagonist Drugs 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 122
101800000989 Oxytocin Proteins 0.000 claims abstract description 35
XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 claims abstract description 35
102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims abstract description 35
XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims abstract description 35
229960001723 oxytocin Drugs 0.000 claims abstract description 35
NXDWUAQXIVWQRL-UHFFFAOYSA-N oxadiazole;pyrrolidine Chemical compound C1CCNC1.C1=CON=N1 NXDWUAQXIVWQRL-UHFFFAOYSA-N 0.000 claims abstract description 28
238000011282 treatment Methods 0.000 claims abstract description 23
102000004279 Oxytocin receptors Human genes 0.000 claims abstract description 20
108090000876 Oxytocin receptors Proteins 0.000 claims abstract description 20
208000006399 Premature Obstetric Labor Diseases 0.000 claims abstract description 17
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 14
206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 11
230000002265 prevention Effects 0.000 claims abstract description 10
230000001404 mediated effect Effects 0.000 claims abstract description 9
208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 4
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003118 aryl group Chemical group 0.000 claims description 67
239000004305 biphenyl Substances 0.000 claims description 61
125000001072 heteroaryl group Chemical group 0.000 claims description 51
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 44
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 37
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 37
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 35
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 32
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 31
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
125000000753 cycloalkyl group Chemical group 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
235000010290 biphenyl Nutrition 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 17
125000005842 heteroatom Chemical group 0.000 claims description 15
125000002252 acyl group Chemical group 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
229920006395 saturated elastomer Polymers 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
230000008569 process Effects 0.000 claims description 10
102000005962 receptors Human genes 0.000 claims description 10
108020003175 receptors Proteins 0.000 claims description 10
125000000304 alkynyl group Chemical group 0.000 claims description 9
230000027455 binding Effects 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
150000004866 oxadiazoles Chemical class 0.000 claims description 7
125000004442 acylamino group Chemical group 0.000 claims description 6
230000003042 antagnostic effect Effects 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
150000002923 oximes Chemical class 0.000 claims description 6
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 5
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 claims description 5
206010036600 Premature labour Diseases 0.000 claims description 5
KRIVWZIPRHSVHX-YJZSVRAESA-N [(2s,4e)-2-[3-(2-hydroxyethyl)-1,2,4-oxadiazol-5-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](C\C(C1)=N/OC)C=1ON=C(CCO)N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 KRIVWZIPRHSVHX-YJZSVRAESA-N 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
208000026440 premature labor Diseases 0.000 claims description 5
125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 4
UOOWZDXZBNPRNB-DEOSSOPVSA-N 1-[4-[5-[(2s)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(N=1)C1CCN(CC1)C(C)=O)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 UOOWZDXZBNPRNB-DEOSSOPVSA-N 0.000 claims description 4
ZCYVMCAHYDRHRY-DEOSSOPVSA-N 1-[4-[[3-[(2s)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]methyl]piperazin-1-yl]ethanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(CN2CCN(CC2)C(C)=O)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZCYVMCAHYDRHRY-DEOSSOPVSA-N 0.000 claims description 4
SRGSUDBDHGIWEG-KRWDZBQOSA-N [(2s)-4-methoxyimino-2-(2-sulfanylidene-3h-1,3,4-oxadiazol-5-yl)pyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1OC(=S)NN=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 SRGSUDBDHGIWEG-KRWDZBQOSA-N 0.000 claims description 4
OOFWBNIVCXOBSW-IBGZPJMESA-N [(2s)-4-methoxyimino-2-(3-methyl-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(C)N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 OOFWBNIVCXOBSW-IBGZPJMESA-N 0.000 claims description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 3
125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 3
LJXIAAKDFSHXQH-QFIPXVFZSA-N 2-[5-[(2s)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl]-1-pyrrolidin-1-ylethanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(CC(=O)N2CCCC2)N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 LJXIAAKDFSHXQH-QFIPXVFZSA-N 0.000 claims description 3
NYCIBBPYIJOSFU-NRFANRHFSA-N 5-[3-[(2S)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]-1H-pyridin-2-one Chemical compound CON=C1CN([C@@H](C1)C1=NOC(=N1)C=1C=NC(=CC=1)O)C(=O)C1=CC=C(C=C1)C1=CC=CC=C1 NYCIBBPYIJOSFU-NRFANRHFSA-N 0.000 claims description 3
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
WGUBFPINURBWTQ-DEOSSOPVSA-N [(2s)-2-(3-benzyl-1,2,4-oxadiazol-5-yl)-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(CC=2C=CC=CC=2)N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 WGUBFPINURBWTQ-DEOSSOPVSA-N 0.000 claims description 3
JXTNHLFHWIKLKB-SFHVURJKSA-N [(2s)-2-[3-(hydroxymethyl)-1,2,4-oxadiazol-5-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(CO)N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 JXTNHLFHWIKLKB-SFHVURJKSA-N 0.000 claims description 3
VKAVWUGMFLJAHN-IBGZPJMESA-N [(2s)-2-[5-(2-hydroxyethyl)-1,2,4-oxadiazol-3-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(CCO)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 VKAVWUGMFLJAHN-IBGZPJMESA-N 0.000 claims description 3
ADHOOZXOWBAZSG-FQEVSTJZSA-N [(2s)-2-[5-[(dimethylamino)methyl]-1,2,4-oxadiazol-3-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(CN(C)C)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ADHOOZXOWBAZSG-FQEVSTJZSA-N 0.000 claims description 3
YXSIQQPYSABBQM-NRFANRHFSA-N [(2s)-2-[5-[2-(dimethylamino)ethyl]-1,2,4-oxadiazol-3-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(CCN(C)C)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 YXSIQQPYSABBQM-NRFANRHFSA-N 0.000 claims description 3
ZXVBDVHURWRABD-DEOSSOPVSA-N [(2s)-2-[5-[4-(hydroxymethyl)phenyl]-1,2,4-oxadiazol-3-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(ON=1)C=1C=CC(CO)=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZXVBDVHURWRABD-DEOSSOPVSA-N 0.000 claims description 3
RAEDBPISOUHNTD-QFIPXVFZSA-N [(2s)-4-methoxyimino-2-(5-pyridin-2-yl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(ON=1)C=1N=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 RAEDBPISOUHNTD-QFIPXVFZSA-N 0.000 claims description 3
JVLSGXYANUTRPM-NRFANRHFSA-N [(2s)-4-methoxyimino-2-(5-thiophen-3-yl-1,2,4-oxadiazol-3-yl)pyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(ON=1)C1=CSC=C1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 JVLSGXYANUTRPM-NRFANRHFSA-N 0.000 claims description 3
OMTXCGPLEVPAMU-QHCPKHFHSA-N [(2s)-4-methoxyimino-2-[3-(1-methylpiperidin-4-yl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(N=1)C1CCN(C)CC1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 OMTXCGPLEVPAMU-QHCPKHFHSA-N 0.000 claims description 3
RWPACKAPRHJJQL-NRFANRHFSA-N [(2s)-4-methoxyimino-2-[3-(5-methyl-1,2-oxazol-3-yl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(N=1)C1=NOC(C)=C1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 RWPACKAPRHJJQL-NRFANRHFSA-N 0.000 claims description 3
WAQKGHONCJIPEV-IBGZPJMESA-N [(2s)-4-methoxyimino-2-[3-(methylsulfonylmethyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(CS(C)(=O)=O)N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 WAQKGHONCJIPEV-IBGZPJMESA-N 0.000 claims description 3
ISBUAAIVQSTNNV-QFIPXVFZSA-N [(2s)-4-methoxyimino-2-[3-(thiophen-2-ylmethyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(CC=2SC=CC=2)N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ISBUAAIVQSTNNV-QFIPXVFZSA-N 0.000 claims description 3
XCIVMJZCLASVJY-VWLOTQADSA-N [(2s)-4-methoxyimino-2-[5-(2-phenoxyethyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(CCOC=2C=CC=CC=2)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 XCIVMJZCLASVJY-VWLOTQADSA-N 0.000 claims description 3
CGVYMEKMVJRTGP-DEOSSOPVSA-N [(2s)-4-methoxyimino-2-[5-(phenoxymethyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(COC=2C=CC=CC=2)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 CGVYMEKMVJRTGP-DEOSSOPVSA-N 0.000 claims description 3
BPHSEGOMDMHBRP-QFIPXVFZSA-N [(2s)-4-methoxyimino-2-[5-(piperazin-1-ylmethyl)-1,2,4-oxadiazol-3-yl]pyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(CN2CCNCC2)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BPHSEGOMDMHBRP-QFIPXVFZSA-N 0.000 claims description 3
PJQSVQZDLXMJGD-IBGZPJMESA-N [4-(2-chlorophenyl)phenyl]-[(2s)-4-methoxyimino-2-(3-methyl-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl]methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(C)N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1Cl PJQSVQZDLXMJGD-IBGZPJMESA-N 0.000 claims description 3
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
125000005251 aryl acyl group Chemical group 0.000 claims description 3
125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
230000000903 blocking effect Effects 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 3
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 3
FJWBHXLJBGWIDH-FQEVSTJZSA-N n-[[3-[(2s)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]methyl]acetamide Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(CNC(C)=O)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 FJWBHXLJBGWIDH-FQEVSTJZSA-N 0.000 claims description 3
QXPZYXPFTSDPAO-VWLOTQADSA-N tert-butyl 4-[5-[(2s)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl]piperidine-1-carboxylate Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(N=1)C1CCN(CC1)C(=O)OC(C)(C)C)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 QXPZYXPFTSDPAO-VWLOTQADSA-N 0.000 claims description 3
BQMQDBGAIAKNJC-QFIPXVFZSA-N [(2s)-2-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(ON=1)C1CCCC1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BQMQDBGAIAKNJC-QFIPXVFZSA-N 0.000 claims description 2
KRIVWZIPRHSVHX-IBGZPJMESA-N [(2s)-2-[3-(2-hydroxyethyl)-1,2,4-oxadiazol-5-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(CCO)N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 KRIVWZIPRHSVHX-IBGZPJMESA-N 0.000 claims description 2
SLFDZMKKALESEV-QHCPKHFHSA-N [(2s)-2-[3-(furan-2-ylmethylsulfonylmethyl)-1,2,4-oxadiazol-5-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1ON=C(CS(=O)(=O)CC=2OC=CC=2)N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 SLFDZMKKALESEV-QHCPKHFHSA-N 0.000 claims description 2
MNWCVVYNHIBRHI-FQEVSTJZSA-N [(2s)-2-[5-(2-methoxyethyl)-1,2,4-oxadiazol-3-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound O1C(CCOC)=NC([C@H]2N(CC(C2)=NOC)C(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 MNWCVVYNHIBRHI-FQEVSTJZSA-N 0.000 claims description 2
BGWOWFYKKGZMKH-DQEYMECFSA-N [(2s)-2-[5-[(2s)-2-hydroxy-2-phenylethyl]-1,2,4-oxadiazol-3-yl]-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(C[C@H](O)C=2C=CC=CC=2)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BGWOWFYKKGZMKH-DQEYMECFSA-N 0.000 claims description 2
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238000003199 nucleic acid amplification method Methods 0.000 description 1
NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
VYCHJEXJHFTAQI-UHFFFAOYSA-N o-prop-2-enylhydroxylamine;hydrate;hydrochloride Chemical compound O.Cl.NOCC=C VYCHJEXJHFTAQI-UHFFFAOYSA-N 0.000 description 1
238000005457 optimization Methods 0.000 description 1
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125000002971 oxazolyl group Chemical group 0.000 description 1
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238000007254 oxidation reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000012026 peptide coupling reagents‎ Substances 0.000 description 1
239000000813 peptide hormone Substances 0.000 description 1
230000009984 peri-natal effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
239000006187 pill Substances 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
239000010318 polygalacturonic acid Substances 0.000 description 1
229920002643 polyglutamic acid Polymers 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
230000002028 premature Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
UXUYQXXOPCMNLU-UHFFFAOYSA-N pyrrolidine;thiadiazole Chemical class C1CCNC1.C1=CSN=N1 UXUYQXXOPCMNLU-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 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
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 1
239000012508 resin bead Substances 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
230000016160 smooth muscle contraction Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000003746 solid phase reaction Methods 0.000 description 1
239000012265 solid product Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000012089 stop solution Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000001975 sympathomimetic effect Effects 0.000 description 1
229940064707 sympathomimetics Drugs 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
235000015523 tannic acid Nutrition 0.000 description 1
229940033123 tannic acid Drugs 0.000 description 1
229920002258 tannic acid Polymers 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
QJHKODUTBJBHQY-JTQLQIEISA-N tert-butyl (2S)-4-methoxyimino-2-(3-methyl-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(=NOC)C[C@H]1C1=NC(C)=NO1 QJHKODUTBJBHQY-JTQLQIEISA-N 0.000 description 1
YJQRTQJTKGRSNY-UIOOFZCWSA-N tert-butyl (4s)-4-[3-[(2s)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate Chemical compound N1([C@@H](CC(C1)=NOC)C=1N=C(ON=1)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 YJQRTQJTKGRSNY-UIOOFZCWSA-N 0.000 description 1
KMBRLTGPGNMNIY-UHFFFAOYSA-N tert-butyl 4-[(z)-n'-hydroxycarbamimidoyl]piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C(\N)=N\O)CC1 KMBRLTGPGNMNIY-UHFFFAOYSA-N 0.000 description 1
SMZKPZXYDDZDJG-UHFFFAOYSA-N tert-butyl n-(cyanomethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC#N SMZKPZXYDDZDJG-UHFFFAOYSA-N 0.000 description 1
USHBSIOIVYNRPC-NRFANRHFSA-N tert-butyl n-[[3-[(2s)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]methyl]carbamate Chemical group N1([C@@H](CC(C1)=NOC)C=1N=C(CNC(=O)OC(C)(C)C)ON=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 USHBSIOIVYNRPC-NRFANRHFSA-N 0.000 description 1
VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003555 thioacetals Chemical class 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
230000002227 vasoactive effect Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Diabetes (AREA)
Gynecology & Obstetrics (AREA)
Pregnancy & Childbirth (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK1555-2003A 2001-06-18 2002-06-14 Oxadiazolové a tiadiazolové deriváty pyrolidínu, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie SK15552003A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01113632		2001-06-18
PCT/EP2002/006629 WO2002102799A2 (fr)	2001-06-18	2002-06-14	Derives de pyrrolidine oxadiazoles et thiadiazoles

Publications (1)

Publication Number	Publication Date
SK15552003A3 true SK15552003A3 (sk)	2004-05-04

Family

ID=8177641

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1555-2003A SK15552003A3 (sk)	2001-06-18	2002-06-14	Oxadiazolové a tiadiazolové deriváty pyrolidínu, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie

Country Status (26)

Country	Link
US (2)	US7115639B2 (fr)
EP (1)	EP1444225B1 (fr)
JP (1)	JP4426284B2 (fr)
KR (1)	KR20040030678A (fr)
CN (1)	CN100564378C (fr)
AR (1)	AR036108A1 (fr)
AU (1)	AU2002319237B2 (fr)
BG (1)	BG108424A (fr)
BR (1)	BR0211030A (fr)
CA (1)	CA2449578C (fr)
CZ (1)	CZ20033475A3 (fr)
EA (1)	EA006212B1 (fr)
EE (1)	EE200400022A (fr)
ES (1)	ES2397305T3 (fr)
HR (1)	HRP20031017A2 (fr)
HU (1)	HUP0400238A2 (fr)
IL (1)	IL159219A0 (fr)
MX (1)	MXPA03011441A (fr)
MY (1)	MY128890A (fr)
NO (1)	NO20035399L (fr)
PL (1)	PL367275A1 (fr)
RS (1)	RS99503A (fr)
SK (1)	SK15552003A3 (fr)
UA (1)	UA75145C2 (fr)
WO (1)	WO2002102799A2 (fr)
ZA (1)	ZA200309402B (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20040030678A (ko)	2001-06-18	2004-04-09	어플라이드 리서치 시스템스 에이알에스 홀딩 엔.브이.	피롤리딘 옥사디아졸 및 티아디아졸 유도체
DE602004024170D1 (de) *	2003-02-27	2009-12-31	Merck Serono Sa Coinsins	Pyrrolidin-derivate als oxytocin antagonisten
DE602005003803T2 (de) *	2004-02-26	2008-12-24	Laboratoires Serono S.A., Coinsins	Verfahren zur herstellung von pyrrolidinoximen
PL1879573T3 (pl)	2005-05-10	2013-05-31	Incyte Holdings Corp	Modulatory 2,3-dioksygenazy indoloaminy i sposoby ich zastosowania
US8450351B2 (en)	2005-12-20	2013-05-28	Incyte Corporation	N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase
CL2007002650A1 (es)	2006-09-19	2008-02-08	Incyte Corp	Compuestos derivados de heterociclo n-hidroxiamino; composicion farmaceutica, util para tratar cancer, infecciones virales y desordenes neurodegenerativos entre otras.
WO2008036642A2 (fr) *	2006-09-19	2008-03-27	Incyte Corporation	N-hydroxyamidinohétérocycles en tant que modulateurs d'indoléamine 2,3-dioxygénase
JP5465720B2 (ja)	2008-07-08	2014-04-09	インサイト・コーポレイション	インドールアミン２，３−ジオキシゲナーゼの阻害剤としての１，２，５−オキサジアゾール
EP2845850A1 (fr) *	2013-09-10	2015-03-11	ObsEva S.A.	Dérivés de pyrrolidine comme antagonistes des récepteurs V1a de vasopressine/oxytocine
ES2799582T3 (es)	2013-11-08	2020-12-18	Incyte Holdings Corp	Proceso para la síntesis de un inhibidor de indoleamina 2,3-dioxigenasa
EP2886107A1 (fr)	2013-12-17	2015-06-24	ObsEva S.A.	Formules orales de dérivés de pyrrolydine
EP3753921A1 (fr)	2014-07-02	2020-12-23	ObsEva S.A.	Cristallin (3z,5s)-5-(hydroxyméthyl)-1-[(2?-méthyl-1,1?-biphényl-4-yl)carbonyl]pyrrolidin-3-one o-méthyloxime et ses procédés d'utilisation
TW202435864A (zh)	2023-02-09	2024-09-16	大陸商上海葆正醫藥科技有限公司	亞胺化合物及其製備方法和應用

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Publication number	Priority date	Publication date	Assignee	Title
FR2722190B1 (fr) *	1994-07-05	1996-10-04	Sanofi Sa	Derives de 1-benzyl-1,3-dihydro-2h-benzimidazol-2-one, leur preparation, les compositions pharmaceutique en contenant
CA2210138A1 (fr)	1995-01-24	1996-08-01	Peter D. Williams	Antagonistes tocolytiques des recepteurs de l'oxytocine
US5756497A (en)	1996-03-01	1998-05-26	Merck & Co., Inc.	Tocolytic oxytocin receptor antagonists
FR2757157B1 (fr) *	1996-12-13	1999-12-31	Sanofi Sa	Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant
EP1176959B1 (fr) *	1999-05-05	2006-03-08	Merck & Co., Inc.	Prolines en tant qu'agents antimicrobiens
DK1268419T3 (da)	2000-03-27	2006-10-02	Applied Research Systems	Farmaceutisk aktive pyrrolidinderivater som BAX-inhibitorer
DE60120661T2 (de) *	2000-03-27	2007-07-05	Applied Research Systems Ars Holding N.V.	Pharmazeutisch wirksame pyrrolidin-derivate als bax-inhibitoren
AU1401902A (en) *	2000-10-17	2002-04-29	Applied Research Systems	Pharmaceutically active sulfanilide derivatives
EP1829861A3 (fr) *	2001-03-20	2009-01-21	Laboratoires Serono SA	Dérivés estérifiés de la pyrrolidine effectifs comme antagonistes de l'oxytocine
KR20040030678A (ko)	2001-06-18	2004-04-09	어플라이드 리서치 시스템스 에이알에스 홀딩 엔.브이.	피롤리딘 옥사디아졸 및 티아디아졸 유도체
ES2249636T3 (es) *	2001-12-20	2006-04-01	Applied Research Systems Ars Holding N.V.	Triazoles como antagonistas de la oxitocina.
UA78058C2 (en) *	2002-07-05	2007-02-15	Applied Research Systems	Pyrrolidine derivative as oxitocin antagonists

2002
- 2002-06-14 KR KR10-2003-7016485A patent/KR20040030678A/ko not_active Ceased
- 2002-06-14 US US10/480,992 patent/US7115639B2/en not_active Expired - Fee Related
- 2002-06-14 EP EP02748785A patent/EP1444225B1/fr not_active Expired - Lifetime
- 2002-06-14 BR BR0211030-0A patent/BR0211030A/pt not_active IP Right Cessation
- 2002-06-14 HR HR20031017A patent/HRP20031017A2/xx not_active Application Discontinuation
- 2002-06-14 CN CNB028159446A patent/CN100564378C/zh not_active Expired - Fee Related
- 2002-06-14 EE EEP200400022A patent/EE200400022A/xx unknown
- 2002-06-14 CA CA2449578A patent/CA2449578C/fr not_active Expired - Fee Related
- 2002-06-14 PL PL02367275A patent/PL367275A1/xx not_active Application Discontinuation
- 2002-06-14 JP JP2003506272A patent/JP4426284B2/ja not_active Expired - Fee Related
- 2002-06-14 IL IL15921902A patent/IL159219A0/xx unknown
- 2002-06-14 EA EA200400049A patent/EA006212B1/ru not_active IP Right Cessation
- 2002-06-14 MX MXPA03011441A patent/MXPA03011441A/es active IP Right Grant
- 2002-06-14 SK SK1555-2003A patent/SK15552003A3/sk not_active Application Discontinuation
- 2002-06-14 CZ CZ20033475A patent/CZ20033475A3/cs unknown
- 2002-06-14 AU AU2002319237A patent/AU2002319237B2/en not_active Ceased
- 2002-06-14 HU HU0400238A patent/HUP0400238A2/hu unknown
- 2002-06-14 ES ES02748785T patent/ES2397305T3/es not_active Expired - Lifetime
- 2002-06-14 WO PCT/EP2002/006629 patent/WO2002102799A2/fr not_active Ceased
- 2002-06-14 RS YU99503A patent/RS99503A/sr unknown
- 2002-06-14 UA UA20031211897A patent/UA75145C2/uk unknown
- 2002-06-18 MY MYPI20022260A patent/MY128890A/en unknown
- 2002-06-21 AR ARP020102353A patent/AR036108A1/es unknown
2003
- 2003-12-03 ZA ZA200309402A patent/ZA200309402B/en unknown
- 2003-12-04 NO NO20035399A patent/NO20035399L/no unknown
- 2003-12-08 BG BG108424A patent/BG108424A/xx unknown
2006
- 2006-06-09 US US11/449,802 patent/US20060229343A1/en not_active Abandoned

Also Published As

Publication number	Publication date
US20060229343A1 (en)	2006-10-12
KR20040030678A (ko)	2004-04-09
JP4426284B2 (ja)	2010-03-03
NO20035399D0 (no)	2003-12-04
CN1639155A (zh)	2005-07-13
WO2002102799A3 (fr)	2003-04-03
NO20035399L (no)	2004-02-17
HRP20031017A2 (en)	2004-04-30
US20040220238A1 (en)	2004-11-04
US7115639B2 (en)	2006-10-03
EP1444225A2 (fr)	2004-08-11
UA75145C2 (en)	2006-03-15
EE200400022A (et)	2004-04-15
JP2004534804A (ja)	2004-11-18
BG108424A (en)	2005-03-31
BR0211030A (pt)	2004-06-22
HK1074204A1 (zh)	2005-11-04
IL159219A0 (en)	2004-06-01
CZ20033475A3 (en)	2004-05-12
AU2002319237B2 (en)	2008-01-03
CA2449578A1 (fr)	2002-12-27
EA200400049A1 (ru)	2004-08-26
EA006212B1 (ru)	2005-10-27
CA2449578C (fr)	2011-12-13
HUP0400238A2 (hu)	2004-07-28
RS99503A (sr)	2006-12-15
AR036108A1 (es)	2004-08-11
ZA200309402B (en)	2004-12-03
CN100564378C (zh)	2009-12-02
PL367275A1 (en)	2005-02-21
WO2002102799A2 (fr)	2002-12-27
ES2397305T3 (es)	2013-03-06
MXPA03011441A (es)	2004-07-01
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