HRP20090489T1 - Hidantoinski derivati korisni kao inhibitori metaloproteinaza - Google Patents
Hidantoinski derivati korisni kao inhibitori metaloproteinaza Download PDFInfo
- Publication number
- HRP20090489T1 HRP20090489T1 HR20090489T HRP20090489T HRP20090489T1 HR P20090489 T1 HRP20090489 T1 HR P20090489T1 HR 20090489 T HR20090489 T HR 20090489T HR P20090489 T HRP20090489 T HR P20090489T HR P20090489 T1 HRP20090489 T1 HR P20090489T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- formula
- phenoxy
- compound
- sulfonyl
- Prior art date
Links
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 title 1
- 150000001469 hydantoins Chemical class 0.000 title 1
- 239000003475 metalloproteinase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 14
- 150000003839 salts Chemical class 0.000 claims abstract 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- -1 {4-[4-(2,2,2-trifluoroethoxy)phenoxy]piperidin-1-yl}sulfonyl Chemical group 0.000 claims 5
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 102000005741 Metalloproteases Human genes 0.000 claims 2
- 108010006035 Metalloproteases Proteins 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- APGCFEZXDHJVGR-QGZVFWFLSA-N (5s)-5-ethyl-5-[[4-[4-(1,1,2,2,2-pentafluoroethoxy)phenoxy]piperidin-1-yl]sulfonylmethyl]imidazolidine-2,4-dione Chemical compound C1CC(OC=2C=CC(OC(F)(F)C(F)(F)F)=CC=2)CCN1S(=O)(=O)C[C@@]1(CC)NC(=O)NC1=O APGCFEZXDHJVGR-QGZVFWFLSA-N 0.000 claims 1
- CPIWFNYGPDHBTN-GOSISDBHSA-N (5s)-5-ethyl-5-[[4-[4-(2,2,2-trifluoroethoxy)phenoxy]piperidin-1-yl]sulfonylmethyl]imidazolidine-2,4-dione Chemical compound C1CC(OC=2C=CC(OCC(F)(F)F)=CC=2)CCN1S(=O)(=O)C[C@@]1(CC)NC(=O)NC1=O CPIWFNYGPDHBTN-GOSISDBHSA-N 0.000 claims 1
- GCLHHSXBTHNZIR-LJQANCHMSA-N (5s)-5-ethyl-5-[[4-[4-(2,2,3,3-tetrafluoropropoxy)phenoxy]piperidin-1-yl]sulfonylmethyl]imidazolidine-2,4-dione Chemical compound C1CC(OC=2C=CC(OCC(F)(F)C(F)F)=CC=2)CCN1S(=O)(=O)C[C@@]1(CC)NC(=O)NC1=O GCLHHSXBTHNZIR-LJQANCHMSA-N 0.000 claims 1
- PIMSLVWUPZQPML-MRXNPFEDSA-N (5s)-5-methyl-5-[[4-[4-(1,1,2,2,2-pentafluoroethoxy)phenoxy]piperidin-1-yl]sulfonylmethyl]imidazolidine-2,4-dione Chemical compound C1CC(OC=2C=CC(OC(F)(F)C(F)(F)F)=CC=2)CCN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O PIMSLVWUPZQPML-MRXNPFEDSA-N 0.000 claims 1
- NWYAUZLEGMZWIR-GOSISDBHSA-N (5s)-5-methyl-5-[[4-[4-(2,2,3,3-tetrafluoropropoxy)phenoxy]piperidin-1-yl]sulfonylmethyl]imidazolidine-2,4-dione Chemical compound C1CC(OC=2C=CC(OCC(F)(F)C(F)F)=CC=2)CCN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O NWYAUZLEGMZWIR-GOSISDBHSA-N 0.000 claims 1
- BRUWSFUBFQYNPG-UHFFFAOYSA-N 1-phenoxypiperidine Chemical compound C1CCCCN1OC1=CC=CC=C1 BRUWSFUBFQYNPG-UHFFFAOYSA-N 0.000 claims 1
- 102000011722 Matrix Metalloproteinase 13 Human genes 0.000 claims 1
- 108010076503 Matrix Metalloproteinase 13 Proteins 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
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
- 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
- A61K31/41—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
- A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
Abstract
Spoj sa formulom (I), naznačen time, daR1 je (2-4C)alkil i je supstituiran sa dvije ili više skupina fluora; iR2 je metil ili etil; ili njegova farmaceutski prihvatljiva sol. Patent sadrži još 12 patentnih zahtjeva.
Description
OPIZ IZUMA
Claims (13)
1. Spoj sa formulom (I),
[image]
naznačen time, da
R1 je (2-)alkil i je supstituiran sa dvije ili više skupina fluora; i
R2 je metil ili etil;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj sa formulom (I), prema zahtjevu 1, naznačen time, da R1 je etil, propil ili butil i je supstituiran sa dvije ili više skupina fluora.
3. Spoj sa formulom (I), prema zahtjevu 1 ili 2, naznačen time, da R1 je etil, propil ili butil i da je supstituiran sa dvije ili šest skupina fluora.
4. Spoj sa formulom (I), prema zahtjevima od 1 do 3, naznačen time, da R1 je CF3CH2-, CF2HCF2-, CF3CF2-, CF3CH2CH2-, CF2HCF2CH2- ili CF3CF2CH2-.
5. Spoj sa formulom (I), prema zahtjevima od 1 do 4, naznačen time, da je izabran iz
5S)-5-metil-5-[({4-[4-(2,2,2-trifluoroetoksi)fenoksi]piperidin-1-il}sulfonil)metil] imidazolidin-2,4-diona;
(5S)-5-etil-5-[({4-[4-(2,2,2-trifluoroetoksi)fenoksi]piperidin-1-il}sulfonil)metil] imidazolidin-2,4-diona;
5S-metil-5-[({4-[4-(1,1,2,2-tetrafluoroetoksi)fenoksi]piperidinil}sulfonil)metil] imidazolidin-2,4-diona;
5S-etil-5-[({4-[4-(1,1,2,2-tetrafluoroetoksi)fenoksi]piperidinil}sulfonil)metil] imidazolidin-2,4-diona;
(5S)-5-metil-5-[({4-[4-(pentafluoroetoksi)fenoksi]piperidin-1-il}sulfonil)metil] imidazolidin-2,4-dion;
(5S)-5-etil-5-[({4-[4-(pentafluoroetoksi)fenoksi]piperidin-1-il}sulfonil)metil] imidazolidin-2,4-diona;
5S-metil-5-[({4-[3,3,3-trifluoropropoksi)fenoksi]piperidin-1-il}sulfonil)metil] imidazolidin-2,4-diona;
5S-etil-5-[({4-[3,3,3-trifluoropropoksi)fenoksi]piperidin-1-il}sulfonil)metil] imidazolidin-2,4-diona;
(5S)-5-metil-5-[({4-[4-(2,2,3,3-tetrafluoropropoksi)fenoksi]-piperidin-1-il}sulfonil) metil]imidazolidin-2,4-diona;
(5S)-5-etil-5-[({4-[4-(2,2,3,3-tetrafluoropropoksi)fenoksi]-piperidin-1-il} sulfonil)metil]imidazolidin-2,4-diona;
(5S)-5-metil-5-[({4-[4-(2,2,3,3,3-pentafluoropropoksi)fenoksi]-piperidin-1-il}sulfonil)metil]imidazolidin-2,4-diona; i
(5S)-5-etil-5-[({4-[4-(2,2,3,3,3-pentafluoropropoksi)fenoksi]-piperidin-1-il} sulfonil)metil]imidazolidin-2,4-diona.
6. Postupak za pripravu spoja formule (I), prema bilo kojem od zahtjeva od 1 do 5 ili njegova farmaceutski prihvatljiva sol, naznačen time, da uključuje reakciju fenoksi piperidina sa formulom (II) sa sulfonil kloridom sa formulom (III),
[image]
pri čemu su R1 i R2 definirani u zahtjevu 1 i gdje je bilo koja funkcionalna skupina zaštićena ukoliko je to potrebno, i
(i) odstranjivanje bilo koje zaštitne skupine; i
(ii) po potrebi formiranje farmaceutski prihvatljive soli.
7. Farmaceutski pripravak, naznačen time, da obuhvaća spoj formule (I) ili njegovu farmaceutski prihvatljivu sol, prema bilo kojem od zahtjeva od 1 do 5 uz sudjelovanje farmaceutski prihvatljivog dodatka, razrjeđivača ili nosača.
8. Spoj sa formulom (I) ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od zahtjeva od 1 do 5, naznačen time, da se koristi u terapiji.
9. Upotreba spoja formule (I) ili njegove farmaceutski prihvatljive soli, prema bilo kojem od zahtjeva od 1 do 5, naznačena time, da se upotrebljava pri proizvodnji lijeka za upotrebu kod tretmana bolesnog stanja koje je uzrokovano sa jednim ili više enzima metaloproteinaza.
10. Upotreba spoja formule (I) ili njegove farmaceutski prihvatljive soli, prema bilo kojem od zahtjeva od 1 do 5, naznačena time, da se upotrebljava pri proizvodnji lijeka za upotrebu kod tretmana bolesnog stanja koje je uzrokovano kolagenazom 3.
11. Upotreba spoja formule (I) ili njegove farmaceutski prihvatljive soli, prema bilo kojem od zahtjeva od 1 do 5, naznačena time, da se upotrebljava pri proizvodnji lijeka za upotrebu kod tretmana osteoartritisa.
12. Spoj sa formulom (I) ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od zahtjeva od 1 do 5, naznačen time, da se upotrebljava pri tretmanu bolesnog stanja uzrokovanog metaloproteinazama.
13. Spoj sa formulom (I) ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od zahtjeva od 1 do 5, naznačen time, da se upotrebljava pri tretmanu reumatoznog artritisa ili osteoartritisa.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0427403.1A GB0427403D0 (en) | 2004-12-15 | 2004-12-15 | Novel compounds I |
PCT/GB2005/004811 WO2006064218A1 (en) | 2004-12-15 | 2005-12-14 | Hydantoin derivatives useful as metalloproteinase inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20090489T1 true HRP20090489T1 (hr) | 2009-10-31 |
Family
ID=34090044
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20090489T HRP20090489T1 (hr) | 2004-12-15 | 2009-09-15 | Hidantoinski derivati korisni kao inhibitori metaloproteinaza |
Country Status (30)
Country | Link |
---|---|
US (1) | US8129412B2 (hr) |
EP (1) | EP1828166B1 (hr) |
JP (1) | JP5042849B2 (hr) |
KR (1) | KR20070090921A (hr) |
CN (1) | CN101080402B (hr) |
AR (1) | AR051797A1 (hr) |
AU (1) | AU2005315459B2 (hr) |
BR (1) | BRPI0519057A2 (hr) |
CA (1) | CA2589525A1 (hr) |
CY (1) | CY1109376T1 (hr) |
DE (1) | DE602005015617D1 (hr) |
DK (1) | DK1828166T3 (hr) |
ES (1) | ES2328836T3 (hr) |
GB (1) | GB0427403D0 (hr) |
HK (1) | HK1108435A1 (hr) |
HR (1) | HRP20090489T1 (hr) |
IL (1) | IL183590A0 (hr) |
MX (1) | MX2007006744A (hr) |
NO (1) | NO20073550L (hr) |
NZ (1) | NZ555684A (hr) |
PL (1) | PL1828166T3 (hr) |
PT (1) | PT1828166E (hr) |
RS (1) | RS51193B (hr) |
RU (1) | RU2388758C2 (hr) |
SA (1) | SA05260406B1 (hr) |
SI (1) | SI1828166T1 (hr) |
TW (1) | TW200634001A (hr) |
UA (1) | UA89067C2 (hr) |
WO (1) | WO2006064218A1 (hr) |
ZA (1) | ZA200705068B (hr) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BRPI0818006B8 (pt) | 2007-10-19 | 2021-05-25 | Boehringer Ingelheim Int | compostos de piperidino-di-hidrotienopirimidinas substituídas, uso dos mesmos e formulações farmacêuticas |
WO2009138777A1 (en) * | 2008-05-12 | 2009-11-19 | Astrazeneca Ab | Process for the preparation of alkoxy-phenoxy-pi peridine |
US7759512B2 (en) | 2008-07-21 | 2010-07-20 | 3M Innovative Properties Company | Aqueous methods for making fluorinated sulfonate esters |
CN102234287B (zh) | 2010-04-26 | 2015-08-05 | 上海阳帆医药科技有限公司 | 硝基咪唑类化合物、其制备方法和用途 |
US9255074B2 (en) | 2010-07-16 | 2016-02-09 | Abbvie Inc. | Process for preparing antiviral compounds |
MY167881A (en) | 2010-07-16 | 2018-09-26 | Abbvie Bahamas Ltd | Process for preparing antiviral compounds |
MX338725B (es) | 2010-07-16 | 2016-04-28 | Abbvie Bahamas Ltd | Ligando de fosfina para reacciones cataliticas. |
US8975443B2 (en) | 2010-07-16 | 2015-03-10 | Abbvie Inc. | Phosphine ligands for catalytic reactions |
HUP1300139A2 (en) | 2013-03-06 | 2014-09-29 | Richter Gedeon Nyrt | Phenoxypiperidine h3 antagonists |
US20160364553A1 (en) * | 2015-06-09 | 2016-12-15 | Intel Corporation | System, Apparatus And Method For Providing Protected Content In An Internet Of Things (IOT) Network |
GB201610056D0 (en) * | 2016-06-09 | 2016-07-27 | Galapagos Nv And Laboratoires Servier Les | Novel compounds and pharmaceutical compositions thereof for the treatment of inflammatory disorders and osteoarthritis |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9919776D0 (en) * | 1998-08-31 | 1999-10-27 | Zeneca Ltd | Compoujnds |
JP2003501414A (ja) * | 1999-06-04 | 2003-01-14 | アストラゼネカ・アクチエボラーグ | メタロプロテイナーゼの阻害剤 |
WO2001062742A1 (en) * | 2000-02-21 | 2001-08-30 | Astrazeneca Ab | Piperidine- and piperazine substituted n-hydroxyformamides as inhibitors of metalloproteinases |
SE0100902D0 (sv) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
SE0301922D0 (sv) | 2003-06-27 | 2003-06-27 | Astrazeneca Ab | Novel compounds |
-
2004
- 2004-12-15 GB GBGB0427403.1A patent/GB0427403D0/en not_active Ceased
-
2005
- 2005-12-14 PT PT05818265T patent/PT1828166E/pt unknown
- 2005-12-14 CA CA002589525A patent/CA2589525A1/en not_active Abandoned
- 2005-12-14 CN CN2005800432057A patent/CN101080402B/zh not_active Expired - Fee Related
- 2005-12-14 NZ NZ555684A patent/NZ555684A/en not_active IP Right Cessation
- 2005-12-14 KR KR1020077013343A patent/KR20070090921A/ko not_active Application Discontinuation
- 2005-12-14 AU AU2005315459A patent/AU2005315459B2/en not_active Ceased
- 2005-12-14 RS RSP-2009/0397A patent/RS51193B/sr unknown
- 2005-12-14 PL PL05818265T patent/PL1828166T3/pl unknown
- 2005-12-14 UA UAA200706159A patent/UA89067C2/ru unknown
- 2005-12-14 SI SI200530774T patent/SI1828166T1/sl unknown
- 2005-12-14 ES ES05818265T patent/ES2328836T3/es active Active
- 2005-12-14 DK DK05818265T patent/DK1828166T3/da active
- 2005-12-14 BR BRPI0519057-6A patent/BRPI0519057A2/pt not_active IP Right Cessation
- 2005-12-14 EP EP05818265A patent/EP1828166B1/en active Active
- 2005-12-14 DE DE602005015617T patent/DE602005015617D1/de active Active
- 2005-12-14 SA SA05260406A patent/SA05260406B1/ar unknown
- 2005-12-14 WO PCT/GB2005/004811 patent/WO2006064218A1/en active Application Filing
- 2005-12-14 JP JP2007546173A patent/JP5042849B2/ja not_active Expired - Fee Related
- 2005-12-14 US US11/793,358 patent/US8129412B2/en not_active Expired - Fee Related
- 2005-12-14 MX MX2007006744A patent/MX2007006744A/es active IP Right Grant
- 2005-12-14 RU RU2007121222/04A patent/RU2388758C2/ru not_active IP Right Cessation
- 2005-12-15 TW TW094144382A patent/TW200634001A/zh unknown
- 2005-12-15 AR ARP050105275A patent/AR051797A1/es not_active Application Discontinuation
-
2007
- 2007-05-31 IL IL183590A patent/IL183590A0/en unknown
- 2007-06-12 ZA ZA200705068A patent/ZA200705068B/xx unknown
- 2007-07-09 NO NO20073550A patent/NO20073550L/no not_active Application Discontinuation
-
2008
- 2008-03-04 HK HK08102383.3A patent/HK1108435A1/xx not_active IP Right Cessation
-
2009
- 2009-09-15 HR HR20090489T patent/HRP20090489T1/hr unknown
- 2009-09-17 CY CY20091100960T patent/CY1109376T1/el unknown
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