NO323969B1 - Farmasoytisk aktive pyrrolidinderivater - Google Patents

Farmasoytisk aktive pyrrolidinderivater Download PDF

Info

Publication number: NO323969B1
Authority: NO; Norway
Prior art keywords: pyrrolidinecarboxamide; methoxyimino; biphenyl; hydroxy; carbonyl
Prior art date: 2000-03-27

Application number

NO20024598A

Other languages

English (en)

Norwegian (no)

Other versions

NO20024598L (no

NO20024598D0 (no

Inventor

Anthony Baxter

Serge Halazy

Anna Quattropani

Alexander Scheer

Matthias Schwarz

Russel J Thomas

Original Assignee

Applied Research Systems

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.)

2000-03-27

Filing date

2002-09-25

Publication date

2007-07-23

2002-09-25 Application filed by Applied Research Systems filed Critical Applied Research Systems

2002-09-25 Publication of NO20024598D0 publication Critical patent/NO20024598D0/no

2002-11-25 Publication of NO20024598L publication Critical patent/NO20024598L/no

2007-07-23 Publication of NO323969B1 publication Critical patent/NO323969B1/no

Links

150000003235 pyrrolidines Chemical class 0.000 title claims description 35
238000000034 method Methods 0.000 claims description 473
-1 dimethylamino, phenylamino, hydroxy, phenoxy Chemical group 0.000 claims description 234
239000004305 biphenyl Chemical group 0.000 claims description 222
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 215
125000001841 imino group Chemical group [H]N=* 0.000 claims description 128
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 73
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 63
125000001424 substituent group Chemical group 0.000 claims description 50
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 47
235000010290 biphenyl Nutrition 0.000 claims description 45
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 42
101800000989 Oxytocin Proteins 0.000 claims description 34
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 description 34
102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims description 34
229960001723 oxytocin Drugs 0.000 claims description 34
125000001072 heteroaryl group Chemical group 0.000 claims description 33
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 description 32
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 28
238000002360 preparation method Methods 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 26
150000002367 halogens Chemical group 0.000 claims description 26
FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 claims description 25
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
102000004279 Oxytocin receptors Human genes 0.000 claims description 23
108090000876 Oxytocin receptors Proteins 0.000 claims description 23
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 21
VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims description 21
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
206010036600 Premature labour Diseases 0.000 claims description 18
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 18
229920006395 saturated elastomer Polymers 0.000 claims description 18
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 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
239000008194 pharmaceutical composition Substances 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 12
208000005171 Dysmenorrhea Diseases 0.000 claims description 11
239000000825 pharmaceutical preparation Substances 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 11
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
150000002923 oximes Chemical class 0.000 claims description 10
206010013935 Dysmenorrhoea Diseases 0.000 claims description 9
208000006399 Premature Obstetric Labor Diseases 0.000 claims description 9
125000000623 heterocyclic group Chemical group 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
208000026440 premature labor Diseases 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 7
230000027455 binding Effects 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000000168 pyrrolyl group Chemical group 0.000 claims description 5
102000005962 receptors Human genes 0.000 claims description 5
108020003175 receptors Proteins 0.000 claims description 5
125000001544 thienyl group Chemical group 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 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 3
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 3
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 3
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 3
125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 3
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
UTMYYLVADKNKHS-UHFFFAOYSA-N CON=C1CCNC1C(N)=O Chemical compound CON=C1CCNC1C(N)=O UTMYYLVADKNKHS-UHFFFAOYSA-N 0.000 claims description 3
125000003368 amide group Chemical group 0.000 claims description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
125000005990 isobenzothienyl group Chemical group 0.000 claims description 3
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
125000005956 isoquinolyl group Chemical group 0.000 claims description 3
125000001786 isothiazolyl group Chemical group 0.000 claims description 3
125000000842 isoxazolyl group Chemical group 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
125000002971 oxazolyl group Chemical group 0.000 claims description 3
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 3
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
125000005493 quinolyl group Chemical group 0.000 claims description 3
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
125000003831 tetrazolyl group Chemical group 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 3
GRMHPNANLFOBAN-SANMLTNESA-N (2s)-4-methylidene-1-(4-phenylbenzoyl)-n-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=C)C(=O)NC=1C=C2C=CC=NC2=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 GRMHPNANLFOBAN-SANMLTNESA-N 0.000 claims description 2
VCHOKELVQXEXCY-QFIPXVFZSA-N (4-hydroxypiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-phenylphenyl)sulfonylpyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCC(CC1)O)S(=O)(=O)C1=CC=C(C=C1)C1=CC=CC=C1 VCHOKELVQXEXCY-QFIPXVFZSA-N 0.000 claims description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 2
RAFOEQLLARZUAM-UHFFFAOYSA-N 4-methoxyiminopyrrolidine-2-carboxamide Chemical compound CON=C1CNC(C(N)=O)C1 RAFOEQLLARZUAM-UHFFFAOYSA-N 0.000 claims description 2
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
230000003042 antagnostic effect Effects 0.000 claims description 2
230000000903 blocking effect Effects 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
150000008366 benzophenones Chemical group 0.000 claims 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
125000005037 alkyl phenyl group Chemical group 0.000 claims 3
125000005874 benzothiadiazolyl group Chemical group 0.000 claims 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
WGIAYBNWTYECJD-UHFFFAOYSA-N 1-ethoxypiperazine Chemical group CCON1CCNCC1 WGIAYBNWTYECJD-UHFFFAOYSA-N 0.000 claims 2
KZHUULABPNPTEO-UHFFFAOYSA-N 2-methoxy-2-phenylacetamide Chemical compound COC(C(N)=O)C1=CC=CC=C1 KZHUULABPNPTEO-UHFFFAOYSA-N 0.000 claims 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
RRVOWCLKRNJCPL-SANMLTNESA-N (2S)-4-(chloromethylidene)-1-(4-phenylbenzoyl)-N-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=CCl)C(=O)NC=1C=C2C=CC=NC2=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 RRVOWCLKRNJCPL-SANMLTNESA-N 0.000 claims 1
ZAXLCZWBAWDNPZ-SANMLTNESA-N (4-hydroxy-4-phenylpiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-pyridin-3-ylbenzoyl)pyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCC(CC1)(C1=CC=CC=C1)O)C(C1=CC=C(C=C1)C=1C=NC=CC=1)=O ZAXLCZWBAWDNPZ-SANMLTNESA-N 0.000 claims 1
NHSFKYKHMRBWGQ-SANMLTNESA-N (4-hydroxy-4-phenylpiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-pyridin-4-ylbenzoyl)pyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCC(CC1)(C1=CC=CC=C1)O)C(C1=CC=C(C=C1)C1=CC=NC=C1)=O NHSFKYKHMRBWGQ-SANMLTNESA-N 0.000 claims 1
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
FFQDGGBBVREZEG-UHFFFAOYSA-N 1-[2-(3-hydroxyphenyl)ethyl]-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound OC=1C=C(C=CC1)CCN1C(CC(C1)=NOC)C(=O)N FFQDGGBBVREZEG-UHFFFAOYSA-N 0.000 claims 1
UKBZKPAADWLERX-UHFFFAOYSA-N 2-(2-anilinoethyl)-4-methoxyimino-1-(4-pyridin-4-ylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N(C1=CC=CC=C1)CCC1(N(CC(C1)=NOC)C(C1=CC=C(C=C1)C1=CC=NC=C1)=O)C(=O)N UKBZKPAADWLERX-UHFFFAOYSA-N 0.000 claims 1
VDMSJBDZBGKULL-UHFFFAOYSA-N 2-ethoxy-2-phenylacetamide Chemical compound CCOC(C(N)=O)C1=CC=CC=C1 VDMSJBDZBGKULL-UHFFFAOYSA-N 0.000 claims 1
ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical group O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
VOLMSPGWNYJHQQ-UHFFFAOYSA-N Pyranone Chemical group CC1=C(O)C(=O)C(O)CO1 VOLMSPGWNYJHQQ-UHFFFAOYSA-N 0.000 claims 1
LMLIZYRZINNREE-QHCPKHFHSA-N [(2S)-1-[4-(3,4-dichlorophenyl)benzoyl]-4-methoxyiminopyrrolidin-2-yl]-[4-(2-hydroxyethyl)piperazin-1-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCN(CC1)CCO)C(=O)C1=CC=C(C=C1)C1=CC(=C(C=C1)Cl)Cl LMLIZYRZINNREE-QHCPKHFHSA-N 0.000 claims 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
125000006267 biphenyl group Chemical group 0.000 claims 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
229960003887 dichlorophen Drugs 0.000 claims 1
125000005805 dimethoxy phenyl group Chemical group 0.000 claims 1
AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 claims 1
125000006501 nitrophenyl group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 544
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 260
238000004128 high performance liquid chromatography Methods 0.000 description 173
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
239000000243 solution Substances 0.000 description 71
OXEUETBFKVCRNP-UHFFFAOYSA-N 9-ethyl-3-carbazolamine Chemical compound NC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 OXEUETBFKVCRNP-UHFFFAOYSA-N 0.000 description 70
JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 60
239000000203 mixture Substances 0.000 description 50
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
238000005481 NMR spectroscopy Methods 0.000 description 44
239000000047 product Substances 0.000 description 44
239000011541 reaction mixture Substances 0.000 description 38
239000000543 intermediate Substances 0.000 description 31
239000002904 solvent Substances 0.000 description 31
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 29
235000019439 ethyl acetate Nutrition 0.000 description 29
MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 28
JKBGXBVHOKKEJO-UHFFFAOYSA-N 2-oxo-6-pentylpyran-3-carbonyl chloride Chemical compound CCCCCC1=CC=C(C(Cl)=O)C(=O)O1 JKBGXBVHOKKEJO-UHFFFAOYSA-N 0.000 description 28
125000005336 allyloxy group Chemical group 0.000 description 28
125000003118 aryl group Chemical group 0.000 description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000004440 column chromatography Methods 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000007787 solid Substances 0.000 description 20
230000015572 biosynthetic process Effects 0.000 description 19
230000000694 effects Effects 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
239000012044 organic layer Substances 0.000 description 17
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
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- 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
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
- A—HUMAN NECESSITIES
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- 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
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
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NO20024598A 2000-03-27 2002-09-25 Farmasoytisk aktive pyrrolidinderivater NO323969B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP00106034		2000-03-27
PCT/EP2001/003171 WO2001072705A1 (en)	2000-03-27	2001-03-20	Pharmaceutically active pyrrolidine derivatives as bax inhibitors

Publications (3)

Publication Number	Publication Date
NO20024598D0 NO20024598D0 (no)	2002-09-25
NO20024598L NO20024598L (no)	2002-11-25
NO323969B1 true NO323969B1 (no)	2007-07-23

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NO20024598A NO323969B1 (no)	2000-03-27	2002-09-25	Farmasoytisk aktive pyrrolidinderivater

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US (2)	US7211601B2 (de)
EP (1)	EP1268419B1 (de)
JP (2)	JP2003528854A (de)
KR (1)	KR100714585B1 (de)
CN (1)	CN1296354C (de)
AR (1)	AR029499A1 (de)
AT (1)	ATE330940T1 (de)
AU (2)	AU5620901A (de)
BG (1)	BG107132A (de)
BR (1)	BR0109900A (de)
CA (1)	CA2401242A1 (de)
CY (1)	CY1105519T1 (de)
CZ (1)	CZ20023243A3 (de)
DE (1)	DE60120940T2 (de)
DK (1)	DK1268419T3 (de)
EA (1)	EA006424B1 (de)
EE (1)	EE200200555A (de)
ES (1)	ES2261404T3 (de)
HK (1)	HK1054031B (de)
HR (1)	HRP20020705A2 (de)
HU (1)	HUP0300994A2 (de)
IL (1)	IL151912A0 (de)
MX (1)	MXPA02009382A (de)
NO (1)	NO323969B1 (de)
NZ (1)	NZ521060A (de)
PL (1)	PL358001A1 (de)
PT (1)	PT1268419E (de)
SI (1)	SI1268419T1 (de)
SK (1)	SK13832002A3 (de)
UA (1)	UA74362C2 (de)
WO (1)	WO2001072705A1 (de)
YU (1)	YU73502A (de)
ZA (1)	ZA200206799B (de)

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AR034897A1 (es)	2001-08-07	2004-03-24	Hoffmann La Roche	Derivados n-monoacilados de o-fenilendiaminas, sus analogos heterociclicos de seis miembros y su uso como agentes farmaceuticos
US7030141B2 (en) *	2001-11-29	2006-04-18	Christopher Franklin Bigge	Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade
US7405234B2 (en)	2002-05-17	2008-07-29	Bristol-Myers Squibb Company	Bicyclic modulators of androgen receptor function
UA78058C2 (en) *	2002-07-05	2007-02-15	Applied Research Systems	Pyrrolidine derivative as oxitocin antagonists
EP1567487A4 (de) *	2002-11-15	2005-11-16	Bristol Myers Squibb Co	Offenkettige, mit prolylharnstoff verwandtemodulatoren der androgenrezeptorfunktion
JP4773335B2 (ja)	2003-02-27	2011-09-14	メルクセローノソシエテアノニム	オキシトシンアンタゴニストとしてのピロリジン誘導体
US7820702B2 (en)	2004-02-04	2010-10-26	Bristol-Myers Squibb Company	Sulfonylpyrrolidine modulators of androgen receptor function and method
DE602005003803T2 (de) *	2004-02-26	2008-12-24	Laboratoires Serono S.A., Coinsins	Verfahren zur herstellung von pyrrolidinoximen
US7696241B2 (en)	2004-03-04	2010-04-13	Bristol-Myers Squibb Company	Bicyclic compounds as modulators of androgen receptor function and method
US7625923B2 (en)	2004-03-04	2009-12-01	Bristol-Myers Squibb Company	Bicyclic modulators of androgen receptor function
EP2379524A1 (de) *	2008-12-18	2011-10-26	Boehringer Ingelheim International GmbH	Inhibitoren des serotonin-5-ht2b-rezeptors
WO2013042782A1 (ja)	2011-09-22	2013-03-28	武田薬品工業株式会社	縮合複素環化合物
EP2845850A1 (de)	2013-09-10	2015-03-11	ObsEva S.A.	Pyrrolidinderivate als Oxytocin/Vasopressin-V1a-Rezeptorantagonisten
EP2886107A1 (de)	2013-12-17	2015-06-24	ObsEva S.A.	Orale Formulierungen von Pyrrolydinderivaten
AU2015283133B2 (en)	2014-07-02	2019-05-16	ObsEva SA	Crystalline (3Z,5S)-5-(hydroxymethyl)-1-[(2'-methyl-1,1'-biphenyl-4-yl)carbonyl]pyrrolidin-3-one O-methyloxime useful in methods of treating conditions related to the OT-R activity
CN114621962B (zh) *	2022-03-21	2024-05-14	广西大学	花生AhBI-1基因VIGS沉默体系
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
CN117044622A (zh) *	2023-09-22	2023-11-14	贵州师范大学	一种无花瓣芥菜型油菜的选育方式

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2001
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- 2001-03-20 HK HK03106333.0A patent/HK1054031B/zh not_active IP Right Cessation
- 2001-03-20 PT PT01929439T patent/PT1268419E/pt unknown
- 2001-03-20 UA UA2002097675A patent/UA74362C2/uk unknown
- 2001-03-20 US US10/239,912 patent/US7211601B2/en not_active Expired - Fee Related
- 2001-03-20 DK DK01929439T patent/DK1268419T3/da active
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- 2001-03-20 SI SI200130566T patent/SI1268419T1/sl unknown
- 2001-03-20 DE DE60120940T patent/DE60120940T2/de not_active Expired - Lifetime
- 2001-03-20 ES ES01929439T patent/ES2261404T3/es not_active Expired - Lifetime
- 2001-03-20 JP JP2001570618A patent/JP2003528854A/ja not_active Withdrawn
- 2001-03-20 AT AT01929439T patent/ATE330940T1/de not_active IP Right Cessation
- 2001-03-20 BR BR0109900-0A patent/BR0109900A/pt not_active IP Right Cessation
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- 2001-03-20 YU YU73502A patent/YU73502A/sh unknown
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- 2001-03-20 CZ CZ20023243A patent/CZ20023243A3/cs unknown
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- 2001-03-20 SK SK1383-2002A patent/SK13832002A3/sk unknown
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2002
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- 2002-09-25 NO NO20024598A patent/NO323969B1/no unknown
2006
- 2006-07-28 CY CY20061101060T patent/CY1105519T1/el unknown
2007
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HK1054031A1 (en)	2003-11-14
YU73502A (sh)	2005-11-28
BG107132A (bg)	2003-04-30
ES2261404T3 (es)	2006-11-16
ZA200206799B (en)	2003-08-26
HUP0300994A2 (hu)	2003-08-28
WO2001072705A1 (en)	2001-10-04
UA74362C2 (uk)	2005-12-15
DE60120940D1 (de)	2006-08-03
US7211601B2 (en)	2007-05-01
AU2001256209B2 (en)	2006-02-16
IL151912A0 (en)	2003-04-10
CA2401242A1 (en)	2001-10-04
NO20024598L (no)	2002-11-25
PT1268419E (pt)	2006-08-31
CZ20023243A3 (cs)	2003-01-15
AR029499A1 (es)	2003-07-02
JP2012149098A (ja)	2012-08-09
US20030212012A1 (en)	2003-11-13
EA200201026A1 (ru)	2003-02-27
NO20024598D0 (no)	2002-09-25
AU5620901A (en)	2001-10-08
KR20020095195A (ko)	2002-12-20
EA006424B1 (ru)	2005-12-29
CY1105519T1 (el)	2010-07-28
CN1419541A (zh)	2003-05-21
KR100714585B1 (ko)	2007-05-07
BR0109900A (pt)	2003-06-03
NZ521060A (en)	2004-05-28
PL358001A1 (en)	2004-08-09
JP5580364B2 (ja)	2014-08-27
ATE330940T1 (de)	2006-07-15
EP1268419B1 (de)	2006-06-21
JP2003528854A (ja)	2003-09-30
US20080167318A1 (en)	2008-07-10
EP1268419A1 (de)	2003-01-02
SK13832002A3 (sk)	2003-03-04
EE200200555A (et)	2004-06-15
HRP20020705A2 (en)	2004-12-31
MXPA02009382A (es)	2003-01-28
SI1268419T1 (sl)	2006-10-31
DK1268419T3 (da)	2006-10-02
DE60120940T2 (de)	2007-01-25
HK1054031B (zh)	2007-05-04
CN1296354C (zh)	2007-01-24

Publication	Publication Date	Title
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