JP2009530396A5 - - Google Patents
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- Publication number
- JP2009530396A5 JP2009530396A5 JP2009501567A JP2009501567A JP2009530396A5 JP 2009530396 A5 JP2009530396 A5 JP 2009530396A5 JP 2009501567 A JP2009501567 A JP 2009501567A JP 2009501567 A JP2009501567 A JP 2009501567A JP 2009530396 A5 JP2009530396 A5 JP 2009530396A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- pyrimido
- tetrahydro
- pyridin
- phenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
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- -1 -NR e R f Chemical group 0.000 claims 104
- 125000000217 alkyl group Chemical group 0.000 claims 81
- 150000001875 compounds Chemical class 0.000 claims 47
- 125000001424 substituent group Chemical group 0.000 claims 28
- 239000002207 metabolite Substances 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 23
- 229940002612 prodrug Drugs 0.000 claims 22
- 239000000651 prodrug Substances 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- GKRCRSXACZSEML-UHFFFAOYSA-N 2-N,2-dimethyl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydro-1H-pyrimido[4,5-d]azepine-2,4-diamine Chemical compound CC1(N=C(C2=C(CCN(CC2)C2=NC=CC=C2C(F)(F)F)N1)N)NC GKRCRSXACZSEML-UHFFFAOYSA-N 0.000 claims 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 10
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000004321 azepin-2-yl group Chemical group [H]N1C([H])=C([H])C([H])=C([H])C([H])=C1* 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 2
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000003725 azepanyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- VCIDLFZYHBUOJH-UHFFFAOYSA-N n-[2-[2-propan-2-yl-4-[4-(trifluoromethyl)anilino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]phenyl]methanesulfonamide Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CC=3)NS(C)(=O)=O)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 VCIDLFZYHBUOJH-UHFFFAOYSA-N 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims 1
- KZMYIZZZFUEQJF-UHFFFAOYSA-N 1-[4-[[2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]ethanone Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)=O)C=C1 KZMYIZZZFUEQJF-UHFFFAOYSA-N 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 1
- SENDDIPZFAVZNJ-UHFFFAOYSA-N 2-[4-[[2-(azepan-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 SENDDIPZFAVZNJ-UHFFFAOYSA-N 0.000 claims 1
- KKICAXULBIYBLY-UHFFFAOYSA-N 2-[4-[[2-(azetidin-1-yl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1NC1=NC(N2CCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 KKICAXULBIYBLY-UHFFFAOYSA-N 0.000 claims 1
- SRLFKTHONBGNEO-UHFFFAOYSA-N 2-[4-[[2-(dimethylamino)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl]amino]phenyl]-2-methylpropanenitrile Chemical compound N=1C(N(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(C)(C)C#N)C=C1 SRLFKTHONBGNEO-UHFFFAOYSA-N 0.000 claims 1
- ZLHFIGAOOZKARB-UHFFFAOYSA-N 2-methoxy-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(OC)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 ZLHFIGAOOZKARB-UHFFFAOYSA-N 0.000 claims 1
- WYACYHGWXXRANR-UHFFFAOYSA-N 2-methylsulfonyl-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(S(=O)(=O)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 WYACYHGWXXRANR-UHFFFAOYSA-N 0.000 claims 1
- MRHHSXHMRZMNIM-UHFFFAOYSA-N 2-piperidin-1-yl-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 MRHHSXHMRZMNIM-UHFFFAOYSA-N 0.000 claims 1
- JOMYUJCRQDDFAR-UHFFFAOYSA-N 2-thiomorpholin-4-yl-n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CCSCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 JOMYUJCRQDDFAR-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 1
- 102000003566 TRPV1 Human genes 0.000 claims 1
- 101150016206 Trpv1 gene Proteins 0.000 claims 1
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 0.000 claims 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims 1
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 229940111134 coxibs Drugs 0.000 claims 1
- 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 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 229960002870 gabapentin Drugs 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 229960001680 ibuprofen Drugs 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- XMMWYCARDXLWNN-UHFFFAOYSA-N n-(4-bromophenyl)-2-propan-2-yl-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)C(F)(F)F)CCC=2C=1NC1=CC=C(Br)C=C1 XMMWYCARDXLWNN-UHFFFAOYSA-N 0.000 claims 1
- VSZWWYRSSXYUJO-UHFFFAOYSA-N n-(4-tert-butylphenyl)-7-(3-methylquinoxalin-2-yl)-2-propan-2-yl-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=NC4=CC=CC=C4N=3)C)CCC=2C=1NC1=CC=C(C(C)(C)C)C=C1 VSZWWYRSSXYUJO-UHFFFAOYSA-N 0.000 claims 1
- YSARDZCQWSGVAK-UHFFFAOYSA-N n-(4-tert-butylphenyl)-7-(6-chloro-5-methylpyrimidin-4-yl)-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound CC1=C(Cl)N=CN=C1N1CCC2=C(NC=3C=CC(=CC=3)C(C)(C)C)N=CN=C2CC1 YSARDZCQWSGVAK-UHFFFAOYSA-N 0.000 claims 1
- HUWDXCSRDAPMOC-UHFFFAOYSA-N n-(4-tert-butylphenyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 HUWDXCSRDAPMOC-UHFFFAOYSA-N 0.000 claims 1
- JPYQYVBZLSMDEY-UHFFFAOYSA-N n-[2-[2-propan-2-yl-4-[4-(trifluoromethyl)anilino]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-7-yl]pyridin-3-yl]methanesulfonamide Chemical compound N=1C(C(C)C)=NC=2CCN(C=3C(=CC=CN=3)NS(C)(=O)=O)CCC=2C=1NC1=CC=C(C(F)(F)F)C=C1 JPYQYVBZLSMDEY-UHFFFAOYSA-N 0.000 claims 1
- HSXSQLHUTDJCHN-UHFFFAOYSA-N n-[4-(trifluoromethyl)phenyl]-7-[3-(trifluoromethyl)pyridin-2-yl]-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC=NC2=C1CCN(C=1C(=CC=CN=1)C(F)(F)F)CC2 HSXSQLHUTDJCHN-UHFFFAOYSA-N 0.000 claims 1
- 229960002009 naproxen Drugs 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 1
- 229940005483 opioid analgesics Drugs 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 229960005489 paracetamol Drugs 0.000 claims 1
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims 1
- 229960001233 pregabalin Drugs 0.000 claims 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 229960004380 tramadol Drugs 0.000 claims 1
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 claims 1
- 0 C*c1nc(CCN(CC2)[Al])c2c(N(*)*)n1 Chemical compound C*c1nc(CCN(CC2)[Al])c2c(N(*)*)n1 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78541506P | 2006-03-21 | 2006-03-21 | |
| US60/785,415 | 2006-03-21 | ||
| PCT/US2007/007166 WO2007109355A2 (en) | 2006-03-21 | 2007-03-21 | 6,7,8, 9 -tetrahydro- 5h- pyrimido [4, 5-d] azepin-4-yl] -amine derivatives as modulators of trpvl for the treatment of pain |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009530396A JP2009530396A (ja) | 2009-08-27 |
| JP2009530396A5 true JP2009530396A5 (https=) | 2010-04-22 |
| JP5232768B2 JP5232768B2 (ja) | 2013-07-10 |
Family
ID=38353855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009501567A Active JP5232768B2 (ja) | 2006-03-21 | 2007-03-21 | Ｔｒｐｖ１のモジュレーターとしてのテトラヒドロ−ピリミドアゼピン |
Country Status (30)
| Country | Link |
|---|---|
| US (3) | US8673895B2 (https=) |
| EP (1) | EP2024368B1 (https=) |
| JP (1) | JP5232768B2 (https=) |
| KR (1) | KR101461376B1 (https=) |
| CN (1) | CN101448835B (https=) |
| AR (1) | AR059985A1 (https=) |
| AU (1) | AU2007227203B2 (https=) |
| BR (1) | BRPI0709034B1 (https=) |
| CA (1) | CA2646977C (https=) |
| CR (1) | CR10387A (https=) |
| DK (1) | DK2024368T3 (https=) |
| EA (1) | EA017069B1 (https=) |
| EC (1) | ECSP088807A (https=) |
| ES (1) | ES2474152T3 (https=) |
| HR (1) | HRP20140664T1 (https=) |
| MX (1) | MX2008012163A (https=) |
| NI (1) | NI200800253A (https=) |
| NO (1) | NO341676B1 (https=) |
| NZ (1) | NZ571343A (https=) |
| PE (1) | PE20080145A1 (https=) |
| PL (1) | PL2024368T3 (https=) |
| PT (1) | PT2024368E (https=) |
| RS (1) | RS53436B (https=) |
| SG (1) | SG177176A1 (https=) |
| SI (1) | SI2024368T1 (https=) |
| TW (1) | TWI440639B (https=) |
| UA (1) | UA92636C2 (https=) |
| UY (1) | UY30229A1 (https=) |
| WO (1) | WO2007109355A2 (https=) |
| ZA (1) | ZA200808975B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1693804B1 (en) * | 1996-09-04 | 2009-11-11 | Intertrust Technologies Corp. | Trusted infrastructure support systems, methods and techniques for secure electronic commerce, electronic transactions, commerce process control and automation, distributed computing and rights management |
| US20080153845A1 (en) * | 2006-10-27 | 2008-06-26 | Redpoint Bio Corporation | Trpv1 antagonists and uses thereof |
| CA2681536A1 (en) * | 2007-03-23 | 2008-10-02 | Pfizer Limited | Pyrimido[4,5-d]azepine derivatives as 5-ht2c agonists |
| US20090156598A1 (en) * | 2007-12-17 | 2009-06-18 | Lebsack Alec D | Imidazolopyrimidine modulators of TRPV1 |
| WO2009078999A1 (en) * | 2007-12-17 | 2009-06-25 | Janssen Pharmaceutica N.V. | Imidazolo-, oxazolo-, and thiazolopyrimidine modulators of trpv1 |
| AR073354A1 (es) * | 2008-07-31 | 2010-11-03 | Genentech Inc | Compuestos de pirimidina, composiciones farmaceuticas y su uso en el tratamiento del cancer. |
| CA2742897A1 (en) * | 2008-11-06 | 2010-05-14 | Astrazeneca Ab | Modulators of amyloid beta. |
| SG176959A1 (en) * | 2009-06-24 | 2012-01-30 | Genentech Inc | Oxo-heterocycle fused pyrimidine compounds, compositions and methods of use |
| CN102712642B (zh) * | 2009-11-12 | 2015-08-12 | 霍夫曼-拉罗奇有限公司 | N-7取代的嘌呤和吡唑并嘧啶化合物、组合物和使用方法 |
| WO2011058027A2 (en) * | 2009-11-12 | 2011-05-19 | F. Hoffmann-La Roche Ag | N-9-substituted purine compounds, compositions and methods of use |
| EP2585216B1 (en) * | 2010-06-23 | 2019-11-20 | Johnson Matthey PLC | Pi-allylpalladium and pi-allylnickel complexes for use as catalysts in carbon-carbon and carbon-nitrogen coupling reactions |
| CN102154494B (zh) * | 2011-03-14 | 2013-01-02 | 中国人民解放军军事医学科学院基础医学研究所 | 一种用于儿童哮喘检测的标志物 |
| WO2014129796A1 (en) | 2013-02-20 | 2014-08-28 | Lg Life Sciences Ltd. | Sphingosine-1-phosphate receptor agonists, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent |
| CN103641762A (zh) * | 2013-12-18 | 2014-03-19 | 中国药科大学 | 一类trpv1/cox-2双重抑制剂、其制备方法及其制备镇痛药物的用途 |
| CN113727758A (zh) * | 2019-03-01 | 2021-11-30 | 锐新医药公司 | 双环杂环基化合物及其用途 |
| BR112022010761A2 (pt) | 2019-12-03 | 2022-08-23 | Lg Chemical Ltd | Agonista do receptor de esfingosina-1-fosfato, método de preparação do mesmo e composição farmacêutica contendo o mesmo como ingrediente ativo |
Family Cites Families (102)
| Publication number | Priority date | Publication date | Assignee | Title |
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