HRP20211605T1 - Spojeni pentaciklični derivati imidazola - Google Patents
Spojeni pentaciklični derivati imidazola Download PDFInfo
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- HRP20211605T1 HRP20211605T1 HRP20211605TT HRP20211605T HRP20211605T1 HR P20211605 T1 HRP20211605 T1 HR P20211605T1 HR P20211605T T HRP20211605T T HR P20211605TT HR P20211605 T HRP20211605 T HR P20211605T HR P20211605 T1 HRP20211605 T1 HR P20211605T1
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- Croatia
- Prior art keywords
- alkyl
- trifluoromethyl
- halogen
- represents hydrogen
- hydroxy
- Prior art date
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- 150000002460 imidazoles Chemical class 0.000 title 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 150000001204 N-oxides Chemical class 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- -1 C1-6Alkoxy Chemical group 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 230000003040 nociceptive effect Effects 0.000 claims 1
- 230000000771 oncological effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Claims (10)
1. Spoj formule (I) ili njegov N-oksid, ili njegova farmaceutski prihvatljiva sol,
[image]
gdje
-X-Q- predstavlja -O-, -O-C(O)-, -O-C(CH-CN)-, -S-, -SO-, -SO2-; ili -N(Rg)-, - N(Rf)-CO-, -N(Rf)-SO2-, -O-CH2-, -CH2-S-, -CH2-SO-, -CH2-SO2-, -N(Rg)-CH2-, -N(Rf)-C(S)-, -N=S(O)(CH3)-, -O-C(=CH2)-ili -S(=N-CN)-, od kojih bilo koja grupa može biti opcionalno supstituirana sa jednim ili više supstituenata izabranih između halogena, (C1-6)alkil, karboksi, trifluorometil, (C2-6)alkilkarbonil, (C2-6)alkoksikarbonil, i hidroksi(C1-6)alkil;
Z predstavlja metilen;
E predstavlja spojeni heteroaromatični sistem prstena izabran između grupa formula (Ea) i (Eb),
[image]
gdje zvjezdica (*) predstavlja mjesto vezivanja E za ostatak molekula;
R1 predstavlja halogen ili cijano; ili aril, heteroaril, (C3-7)cikloalkil-heteroaril, (C3-7)heterocikloalkil-heteroaril, (C4-9)heterobicikloalkil-heteroaril, (C3-7)heterocikloalkil, (C3-7)heterocikloalkenil, ili (C3-7)heterocikloalkenil-aril, od kojih bilo koja grupa može biti opcionalno supstituirana sa jednim, dva ili tri supstituenta izabranih između halogena, cijano, cijano(C1-6)alkil, C1-6 alkil, difluorometil, trifluorometil, hidroksi, (hidroksi)(C1-6)alkil, amino, (amino)(C1-6) alkil, C1-6alkoksi, (C1-6) alkoksi(C1-6)alkil, C2-6 alkilkarbonil, C2-6 alkoksikarbonil, (C2-6) alkoksikarbonil-amino-C1-6 alkil, fosfat(C1-6)alkil, C1-6 alkiltio, C1-6 alkilsulfonil, okso, (C1-6)alkilsulfoksiminil, (C1-6)alkilsulfonil-amino-, di(C1-6)alkilamino (C1-6)alkil, (C2-6)alkilkarbonilamino(C1-6)alkil, di(C1-6)alkenilamino (C1-6)alkil, (C2-6)alkilkarbonilamino(C1-6)alkil, C1-6 alkilsulfonil-amino-C1-6 alkil, tetrahidrofuranil, sulfat (C1-6)alkil, i karboksi-(Ci-6)alkil-karboniloksi-(C1-6 )alkil;
R2 predstavlja vodik ili halogen;
R3 predstavlja vodik ili trifluorometil;
R4 predstavlja vodik ili trifluorometil;
R5 predstavlja halogen, -ORa, difluorometoksi ili trifluorometoksi;
R6 predstavlja vodik, halogen ili trifluorometil;
R7 predstavlja vodik ili trifluorometil;
R8 predstavlja vodik, halogen ili trifluorometil;
R12 predstavlja vodik ili C1-6 alkil;
Ra predstavlja C1-6 alkil;
Rf predstavlja vodik; ili C1-6 alkil, gdje grupa može biti opcionalno supstituirana sa jednim ili više supstituenta izabranih između trifluorometila, karboksi i hidroksi; i
Rg predstavlja vodik; ili C1-6 alkil, -CO-(C1-6)alkil, -SO2-(C1-6)alkil, -CO-(C3-7)heterocikloalkil, -SO2-(C3-7)cikloalkil, - SO2-aril, -SO2-heteroaril, heteroaril ili (C2-6)alkoksikarbonil, od kojih bilo koja grupa može biti opcionalno supstituirana jednim ili više supstituenata izabranih između halogena, C1-6 alkil, karboksi, C1-6 alkoksikarbonil, trifluorometil, C4-9 heterobicikloalkil, (C1-6 alkil)sulfonil, tri(C1-6 alkil)sililoksi, hidroksi i (C1-6)alkoksi.
2. Spoj prema patentnom zahtjevu 1 prikazano formulom (IB) ili (IC), ili njegov N-oksid , ili njegova farmaceutski prihvatljiva sol,
[image]
gdje
Z, -X-Q-, R1, R2, R3, R4, R5, R6, R7, R8, R12, Rg i Rf su kao što je definirano u patentnom zahtjevu 1;
[image]
gdje Z, -X-Q-, R1, R2, R3, R4, R5, R6, R7, R8, R12, Rg i Rf su kao što je definirano u patentnom zahtjevu 1.
3. Spoj prema patentnom zahtjevu 1 u kome -X-Q-predstavlja -O-,-O-C(O)-, -O-C(CH-CN)-, -S-, -SO-, -SO2-, -N(H)-, -N(CO-CH3)-, -N(SO2-CH3)-, -N(CH2-CO-O-CH2-CH3)-, -N[(CO-CH2-(3,7-dioksa-9-azabiciklo[3.3.1]non-9-il)]-, -N[CO-(azetidin-3-il)]-, -N[CO-(metilsulfonil)azetidin-3-il)]-, -N(CH2-COOH)-, -N[(terc-butil)(dimetil)sililoksietil]-, -N(SO2-piridin-3-il)-, -N-(SO2-ciklopropil)-, -N(CH3)-CH2-, -N(CH2-CH2-OH)-, -N(SO2-fenil)-, -N[SO2-(6-metoksi-piridin-3-il)]-, -N(H)-CO-, -N(CH3)-CO-, -N(CH2CH3)-CO-, -N(CH(CH3)2)-CO-, -N(CH2-COOH)-CO-, -N(CH2-CF3)-CO-, -N(CH2-CH2-OH)-CO-, -N(CH2-C(OH)(CH3)2)-CO-, -N(CD3)-CO-, -N(H)-CH2-, -N(CH2-COOH)-CH2-, -N(H)-CH(CF3)-, -N(H)-CH(CH3)-, -N(H)-C(S)-, -N(CO-CH3)-CH(CH3)-, -N(SO2-CH3)-CH2-, -N(CO-CH3)-CH(CH3)-, -N=S(O)(CH3)-, -O-CH(CF3)-, -CH(COOC2H5)-S-, -CH2-SO-, -CH2-SO2-, -CH(C(OH)(CH3)2)-S-, -CH(CH2OH)-S-, -O-C(=CH2)-, -N[S(O)2-(piridin-1H-2-on)]-, -N(H)-SO2-, -N(pirimidinil)-, -N(COOC2H5)-, -S(=N-CN)-ili -N(C2H5)-CO-.
4. Spoj prema patentnom zahtjevu 1 prikazan formulom (IIB) ili njegov N-oksid, ili njegova farmaceutski prihvatljiva sol,
[image]
gdje R1, R2 , R3, R4, R5, R6, R7, R8, i Rf su kao što je definirano u patentnom zahtjevu 1.
5. Spoj prema patentnom zahtjevu 1 prikazano formulom (IIB-A), ili njegov N-oksid, ili njegova farmaceutski prihvatljiva sol,
[image]
gdje
R1 predstavlja aril ili heteroaril, od kojih bilo koja grupa može biti opcionalno supstituirana sa jednim, dva ili tri supstituenta izabranih između halogena, cijano, cijano(C1-6)alkil, C1-6 alkil, difluorometil, trifluorometil, hidroksi, (hidroksi)(C1-6)alkil, amino, (amino)(C1-6) alkil, C1-6 alkoksi, (C1-6) alkoksi(C1-6)alkil, C2-6 alkilkarbonil, C2-6 alkoksikarbonil, (C2-6) alkoksikarbonilamino-C1-6 alkil, fosfat(C1-6)alkil, C1-6 alkiltio, C1-6 alkilsulfonil, okso, (C1-6)alkilsulfoksiminil, (C1-6)alkilsulfonil-amino-, di(C1-6)alkilamino (C1-6)alkil, (C2-6)alkilkarbonilamino(C1-6)alkil, di(C1-6)alkenilamino (C1-6)alkil, (C2-6)alkilkarbonilamino(C1-6)alkil, C1-6 alkilsulfonilamino-C1-6 alkil, tetrahidrofuranil, sulfat(C1-6)alkil, i karboksi-(C1-6)alkil-karboniloksi-(C1-6)alkil;
R2 predstavlja vodik ili halogen;
R5 predstavlja halogen, -ORa, difluorometoksi ili trifluorometoksi;
Ra predstavlja C1-6 alkil; i
Rf predstavlja vodik; ili C1-6 alkil, gdje grupa može biti opcionalno supstituirana sa jednim ili više supstituenta izabranih između trifluorometil, karboksi i hidroksi.
6. Spoj prema patentnom zahtjevu 5 prikazan formulom (IIB-AB-A), njegov N-oksid, ili njegova farmaceutski prihvatljiva sol,
[image]
gdje
R9 predstavlja amino(C1-6)alkil, hidroksi(C1-6)alkil, ili (C1-6) alkoksi(C1-6)alkil;
R10 predstavlja vodik ili C1-6 alkil;
R2, R5 i Rf su kao što je definirano u patentnom zahtjevu 5; i
W predstavlja N ili C-H; i
gdje R9 poželjno predstavlja 2-hidroksi-prop-2-il.
7. Spoj prema patentnom zahtjevu 6 gdje W predstavlja N; i/ili
gdje R10 predstavlja vodik.
8. Spoj formule (I) prema bilo kojem od prethodnih patentnih zahtjeva, ili njegov N-oksid, ili njegova farmaceutski prihvatljiva sol, za upotrebu u terapiji.
9. Spoj formule (I) prema bilo kojem od prethodnih patentnih zahtjeva ili njegov N-oksid, ili njegova farmaceutski prihvatljiva sol, za upotrebu u liječenju i/ili prevenciji upalnog ili autoimunog poremećaja, neurološkog ili neurodegenerativnog poremećaja, boli ili nociceptivnog poremećaja, kardiovaskularnog poremećaja, metaboličkog poremećaja, očnog poremećaja ili onkološkog poremećaja.
10. Farmaceutski sastav koji sadrži spoj formule (I) prema bilo kojem od prethodnih patentnih zahtjeva ili njegov N-oksid, ili njegovu farmaceutski prihvatljivu sol, zajedno sa farmaceutski prihvatljivim nosačem.
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| Application Number | Priority Date | Filing Date | Title |
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| EP14290299 | 2014-10-03 | ||
| EP15162641 | 2015-04-07 | ||
| EP15171036 | 2015-06-08 | ||
| EP15771976.6A EP3201196B1 (en) | 2014-10-03 | 2015-10-02 | Fused pentacyclic imidazole derivatives |
| PCT/EP2015/072868 WO2016050975A1 (en) | 2014-10-03 | 2015-10-02 | Fused pentacyclic imidazole derivatives |
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| HUE056133T2 (hu) * | 2014-10-03 | 2022-01-28 | UCB Biopharma SRL | Fuzionált pentaciklusos imidazol-származékok |
| AR104291A1 (es) | 2015-04-17 | 2017-07-12 | Abbvie Inc | Moduladores tricíclicos de la señalización por tnf |
| WO2016168633A1 (en) | 2015-04-17 | 2016-10-20 | Abbvie Inc. | Indazolones as modulators of tnf signaling |
| WO2016168638A1 (en) | 2015-04-17 | 2016-10-20 | Abbvie Inc. | Indazolones as modulators of tnf signaling |
| GB201510758D0 (en) | 2015-06-18 | 2015-08-05 | Ucb Biopharma Sprl | Novel TNFa structure for use in therapy |
| EP3436460B1 (en) | 2016-04-01 | 2021-08-18 | UCB Biopharma SRL | Fused pentacyclic imidazole derivatives as modulators of tnf activity |
| JP6968089B2 (ja) * | 2016-04-01 | 2021-11-17 | ユーシービー バイオファルマ エスアールエル | Ｔｎｆ活性のモジュレーターとしての縮合六環式イミダゾール誘導体 |
| WO2017167996A1 (en) | 2016-04-01 | 2017-10-05 | Ucb Biopharma Sprl | Fused pentacyclic imidazole derivatives as modulators of tnf activity |
| CN109195969B (zh) * | 2016-04-01 | 2021-12-21 | Ucb生物制药私人有限公司 | 作为tnf活性调节剂的稠合五环咪唑衍生物 |
| GB201620948D0 (en) | 2016-12-09 | 2017-01-25 | Ucb Biopharma Sprl | Therapeutic agents |
| GB201621907D0 (en) | 2016-12-21 | 2017-02-01 | Ucb Biopharma Sprl And Sanofi | Antibody epitope |
| CA3055863A1 (en) * | 2017-03-15 | 2018-09-20 | Ucb Biopharma Sprl | Fused pentacyclic imidazole derivatives as modulators of tnf activity |
| LT3615534T (lt) * | 2017-04-25 | 2021-11-25 | UCB Biopharma SRL | Sulieti pentacikliniai imidazolo dariniai kaip tnf aktyvumo moduliatoriai |
| WO2020084008A1 (en) | 2018-10-24 | 2020-04-30 | UCB Biopharma SRL | Fused pentacyclic imidazole derivatives as modulators of tnf activity |
| CN113683505A (zh) * | 2021-09-29 | 2021-11-23 | 厦门大华本安化工安全研究院有限公司 | 一种含氧代环丁基的羧酸酯类化合物的制备方法 |
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| EP0449649A3 (en) | 1990-03-30 | 1992-09-02 | Arizona Board Of Regents, Arizona State University | Antineoplastic quinones and methods of using same |
| FR2832711B1 (fr) | 2001-11-26 | 2004-01-30 | Warner Lambert Co | Derives de triazolo [4,3-a] pyrido [2,3-d] pyrimidin-5-ones, compositions les contenant, procede de preparation et utilisation |
| CA2517281A1 (en) | 2003-03-10 | 2004-10-14 | Pfizer Inc. | Phosphate/sulfate ester compounds and pharmaceutical compositions for inhibiting protein interacting nima (pin1) |
| DE102008030206A1 (de) | 2008-06-25 | 2009-12-31 | Bayer Schering Pharma Aktiengesellschaft | 3-Cyanoalky- und 3-Hydroxyalkyl-Indole und ihre Verwendung |
| AR088728A1 (es) | 2011-03-25 | 2014-07-02 | Bristol Myers Squibb Co | Moduladores de lxr como prodroga de imidazol |
| JP5977344B2 (ja) | 2011-06-20 | 2016-08-24 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | ジャイレースおよびトポイソメラーゼ阻害剤のリン酸エステル |
| CN104428293B (zh) * | 2012-06-11 | 2018-06-08 | Ucb生物制药私人有限公司 | 调节TNFα的苯并咪唑类 |
| ES2689429T3 (es) * | 2012-07-13 | 2018-11-14 | Ucb Biopharma Sprl | Derivados de imidazopiridina como moduladores de actividad de TNF |
| GB201212513D0 (en) | 2012-07-13 | 2012-08-29 | Ucb Pharma Sa | Therapeutic agents |
| PE20160546A1 (es) | 2013-10-25 | 2016-05-26 | Novartis Ag | Compuestos derivados de piridilo biciclicos fusionados a anillo como inhibidores de fgfr4 |
| GB201321729D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| GB201321728D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| ES2957761T3 (es) | 2014-04-15 | 2024-01-25 | Vertex Pharma | Composiciones farmacéuticas para el tratamiento de enfermedades mediadas por el regulador de la conductancia transmembrana de fibrosis quística |
| HUE056133T2 (hu) * | 2014-10-03 | 2022-01-28 | UCB Biopharma SRL | Fuzionált pentaciklusos imidazol-származékok |
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