NO783767L - Analogifremgangsmaate for fremstilling av terapeutisk aktive erytromycinderivater - Google Patents

Analogifremgangsmaate for fremstilling av terapeutisk aktive erytromycinderivater

Info

Publication number: NO783767L
Authority: NO; Norway
Prior art keywords: group; carbon atoms; general formula; hydrogen atom; linear
Prior art date: 1977-11-10

Application number

NO783767A

Other languages

English (en)

Norwegian (no)

Inventor

Eberhard Woitun

Bernd Wetzel

Roland Maier

Wolfgang Reuter

Uwe Lechner

Rolf G Werner

Hanns Goeth

Original Assignee

Thomae Gmbh Dr K

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.)

1977-11-10

Filing date

1978-11-09

Publication date

1979-05-11

1978-11-09 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1979-05-11 Publication of NO783767L publication Critical patent/NO783767L/no

Links

238000000034 method Methods 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 5
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 title description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 47
-1 pyrrolidino, morpholino, thiomorpholino, piperazino Chemical group 0.000 claims description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 10
125000004663 dialkyl amino group Chemical group 0.000 claims description 10
229960003276 erythromycin Drugs 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
150000007522 mineralic acids Chemical class 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
235000005985 organic acids Nutrition 0.000 claims description 4
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
125000006524 alkoxy alkyl amino group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 1
238000002844 melting Methods 0.000 description 76
230000008018 melting Effects 0.000 description 76
238000006243 chemical reaction Methods 0.000 description 58
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
XCLJRCAJSCMIND-JCTYMORFSA-N (9S)-erythromycyclamine Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)[C@@H](N)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 XCLJRCAJSCMIND-JCTYMORFSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
239000002253 acid Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
MTEQLYDOCFPCAX-UHFFFAOYSA-N 2-chloro-n,n-dimethylpyrimidin-4-amine Chemical compound CN(C)C1=CC=NC(Cl)=N1 MTEQLYDOCFPCAX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\O)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
NPTGVVKPLWFPPX-UHFFFAOYSA-N 2-amino-4-chloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(N)=N1 NPTGVVKPLWFPPX-UHFFFAOYSA-N 0.000 description 1
GIDYFOJSPIYOND-UHFFFAOYSA-N 2-chloro-4,6-dimethyl-5-phenylpyrimidine Chemical compound CC1=NC(Cl)=NC(C)=C1C1=CC=CC=C1 GIDYFOJSPIYOND-UHFFFAOYSA-N 0.000 description 1
BDXYNMVQMBCTDB-UHFFFAOYSA-N 2-chloro-4-methoxypyrimidine Chemical compound COC1=CC=NC(Cl)=N1 BDXYNMVQMBCTDB-UHFFFAOYSA-N 0.000 description 1
PKJCRJDAWHFWHT-UHFFFAOYSA-N 2-chloro-4-methyl-5-nitro-6-piperidin-1-ylpyrimidine Chemical compound CC1=NC(Cl)=NC(N2CCCCC2)=C1[N+]([O-])=O PKJCRJDAWHFWHT-UHFFFAOYSA-N 0.000 description 1
KYWPHKLNTWDUPZ-UHFFFAOYSA-N 2-chloro-4-piperidin-1-ylpyrimidine Chemical compound ClC1=NC=CC(N2CCCCC2)=N1 KYWPHKLNTWDUPZ-UHFFFAOYSA-N 0.000 description 1
SLATYZNORJSBJV-UHFFFAOYSA-N 2-chloro-6-methylpyrido[3,2-d]pyrimidin-4-amine Chemical compound N1=C(Cl)N=C(N)C2=NC(C)=CC=C21 SLATYZNORJSBJV-UHFFFAOYSA-N 0.000 description 1
YYCMHLNHTHIAKV-UHFFFAOYSA-N 2-chloro-n,n,5,6-tetramethylthieno[2,3-d]pyrimidin-4-amine Chemical compound CN(C)C1=NC(Cl)=NC2=C1C(C)=C(C)S2 YYCMHLNHTHIAKV-UHFFFAOYSA-N 0.000 description 1
ZSEJTTDZSKKBER-UHFFFAOYSA-N 2-chloro-n,n-dimethylpyrido[3,2-d]pyrimidin-4-amine Chemical compound C1=CN=C2C(N(C)C)=NC(Cl)=NC2=C1 ZSEJTTDZSKKBER-UHFFFAOYSA-N 0.000 description 1
DTTPDWSQHPZGEY-UHFFFAOYSA-N 2-chloro-n,n-dimethylquinazolin-4-amine Chemical compound C1=CC=C2C(N(C)C)=NC(Cl)=NC2=C1 DTTPDWSQHPZGEY-UHFFFAOYSA-N 0.000 description 1
KLUTWHQEJLDLEQ-UHFFFAOYSA-N 2-chloro-n,n-dimethylthieno[3,2-d]pyrimidin-4-amine Chemical compound CN(C)C1=NC(Cl)=NC2=C1SC=C2 KLUTWHQEJLDLEQ-UHFFFAOYSA-N 0.000 description 1
CBGPQFOKFNIGIL-UHFFFAOYSA-N 2-chloro-n-(2-methoxyethyl)pyrimidin-4-amine Chemical compound COCCNC1=CC=NC(Cl)=N1 CBGPQFOKFNIGIL-UHFFFAOYSA-N 0.000 description 1
LTFNDXISRKPGHC-UHFFFAOYSA-N 2-chloro-n-propan-2-ylpyrimidin-4-amine Chemical compound CC(C)NC1=CC=NC(Cl)=N1 LTFNDXISRKPGHC-UHFFFAOYSA-N 0.000 description 1
XUTFGEBBHSHDLA-UHFFFAOYSA-N 2-chloro-n-propylthieno[3,2-d]pyrimidin-4-amine Chemical compound CCCNC1=NC(Cl)=NC2=C1SC=C2 XUTFGEBBHSHDLA-UHFFFAOYSA-N 0.000 description 1
LPBDZVNGCNTELM-UHFFFAOYSA-N 2-chloropyrimidin-4-amine Chemical compound NC1=CC=NC(Cl)=N1 LPBDZVNGCNTELM-UHFFFAOYSA-N 0.000 description 1
UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
IAGROJPXACRRDT-UHFFFAOYSA-N 2-piperidin-1-ylpyrimidine Chemical compound C1CCCCN1C1=NC=CC=N1 IAGROJPXACRRDT-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
HKQMXHKNXRNUCF-UHFFFAOYSA-N 4-(2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine Chemical compound C=12SC=CC2=NC(Cl)=NC=1N1CCOCC1 HKQMXHKNXRNUCF-UHFFFAOYSA-N 0.000 description 1
PYOSAEIKXWOYFE-UHFFFAOYSA-N 4-(4-chloro-7-phenylpyrimido[4,5-d]pyrimidin-2-yl)morpholine Chemical compound N=1C=C2C(Cl)=NC(N3CCOCC3)=NC2=NC=1C1=CC=CC=C1 PYOSAEIKXWOYFE-UHFFFAOYSA-N 0.000 description 1
JORDJRAQJPQYLB-UHFFFAOYSA-N 4-(4-chloropyrimidin-2-yl)morpholine Chemical compound ClC1=CC=NC(N2CCOCC2)=N1 JORDJRAQJPQYLB-UHFFFAOYSA-N 0.000 description 1
AXIGLJLVIKMORQ-UHFFFAOYSA-N 4-(4-chloropyrimidin-2-yl)thiomorpholine Chemical compound ClC1=CC=NC(N2CCSCC2)=N1 AXIGLJLVIKMORQ-UHFFFAOYSA-N 0.000 description 1
RYMRCBDVPGPBQI-UHFFFAOYSA-N 4-(4-chlorothieno[2,3-d]pyrimidin-2-yl)morpholine Chemical compound N=1C=2SC=CC=2C(Cl)=NC=1N1CCOCC1 RYMRCBDVPGPBQI-UHFFFAOYSA-N 0.000 description 1
WQHNEXFJEUSQPP-UHFFFAOYSA-N 4-chloro-2-(dimethylamino)-6,7-dihydro-5h-pyrido[3,4-d]pyrimidin-8-one Chemical compound C1CN=C(O)C2=NC(N(C)C)=NC(Cl)=C21 WQHNEXFJEUSQPP-UHFFFAOYSA-N 0.000 description 1
YNFXOUGXAYOHHA-UHFFFAOYSA-N 4-chloro-2-n,2-n,7-n,7-n-tetramethylpyrimido[4,5-d]pyrimidine-2,7-diamine Chemical compound ClC1=NC(N(C)C)=NC2=NC(N(C)C)=NC=C21 YNFXOUGXAYOHHA-UHFFFAOYSA-N 0.000 description 1
DFNTXDDYVXGSLY-UHFFFAOYSA-N 4-chloro-2-piperidin-1-ylpyrimidine Chemical compound ClC1=CC=NC(N2CCCCC2)=N1 DFNTXDDYVXGSLY-UHFFFAOYSA-N 0.000 description 1
UDBZUFZWXJJBAL-UHFFFAOYSA-N 4-chloro-5-methylpyrimidin-2-amine Chemical compound CC1=CN=C(N)N=C1Cl UDBZUFZWXJJBAL-UHFFFAOYSA-N 0.000 description 1
RRYMNVKVNNTFAQ-UHFFFAOYSA-N 4-chloro-6-ethoxy-n,n-dimethyl-1,3,5-triazin-2-amine Chemical compound CCOC1=NC(Cl)=NC(N(C)C)=N1 RRYMNVKVNNTFAQ-UHFFFAOYSA-N 0.000 description 1
RAASKXZZDRRVPI-UHFFFAOYSA-N 4-chloro-6-ethyl-n,n-dimethylpyrimidin-2-amine Chemical compound CCC1=CC(Cl)=NC(N(C)C)=N1 RAASKXZZDRRVPI-UHFFFAOYSA-N 0.000 description 1
KLJGSQVYUGQOAW-UHFFFAOYSA-N 4-chloro-6-methoxypyrimidine Chemical compound COC1=CC(Cl)=NC=N1 KLJGSQVYUGQOAW-UHFFFAOYSA-N 0.000 description 1
SLQVWRZBKSLQRW-UHFFFAOYSA-N 4-chloro-n,n,5,6-tetramethylpyrimidin-2-amine Chemical compound CN(C)C1=NC(C)=C(C)C(Cl)=N1 SLQVWRZBKSLQRW-UHFFFAOYSA-N 0.000 description 1
IUYMUWLYDYYIHH-UHFFFAOYSA-N 4-chloro-n,n,5-trimethylpyrimidin-2-amine Chemical compound CN(C)C1=NC=C(C)C(Cl)=N1 IUYMUWLYDYYIHH-UHFFFAOYSA-N 0.000 description 1
JDYDIHVYOFAERC-UHFFFAOYSA-N 4-chloro-n,n,6-trimethylpyrimidin-2-amine Chemical compound CN(C)C1=NC(C)=CC(Cl)=N1 JDYDIHVYOFAERC-UHFFFAOYSA-N 0.000 description 1
MVNADFZYWTVRNK-UHFFFAOYSA-N 4-chloro-n,n-diethylpyrimidin-2-amine Chemical compound CCN(CC)C1=NC=CC(Cl)=N1 MVNADFZYWTVRNK-UHFFFAOYSA-N 0.000 description 1
UGOSXKFKKUEJTH-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-5-pentylpyrimidin-2-amine Chemical compound CCCCCC1=CN=C(N(C)C)N=C1Cl UGOSXKFKKUEJTH-UHFFFAOYSA-N 0.000 description 1
CLZUDZKHBKRRIJ-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-5-phenylpyrimidin-2-amine Chemical compound ClC1=NC(N(C)C)=NC=C1C1=CC=CC=C1 CLZUDZKHBKRRIJ-UHFFFAOYSA-N 0.000 description 1
YDCHWELRUMPAKH-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-6-phenylpyrimidin-2-amine Chemical compound CN(C)C1=NC(Cl)=CC(C=2C=CC=CC=2)=N1 YDCHWELRUMPAKH-UHFFFAOYSA-N 0.000 description 1
HOHOTLHTQGRVMC-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-6-piperidin-1-yl-1,3,5-triazin-2-amine Chemical compound CN(C)C1=NC(Cl)=NC(N2CCCCC2)=N1 HOHOTLHTQGRVMC-UHFFFAOYSA-N 0.000 description 1
XWPZRYPBAHYNBP-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-6-propan-2-ylpyrimidin-2-amine Chemical compound CC(C)C1=CC(Cl)=NC(N(C)C)=N1 XWPZRYPBAHYNBP-UHFFFAOYSA-N 0.000 description 1
CJKPZNGEVQSIND-UHFFFAOYSA-N 4-chloro-n,n-dimethylpyrimidin-2-amine Chemical compound CN(C)C1=NC=CC(Cl)=N1 CJKPZNGEVQSIND-UHFFFAOYSA-N 0.000 description 1
AGRBXJZVFKROKB-UHFFFAOYSA-N 4-chloro-n-(2-methoxyethyl)pyrimidin-2-amine Chemical compound COCCNC1=NC=CC(Cl)=N1 AGRBXJZVFKROKB-UHFFFAOYSA-N 0.000 description 1
UKLSJMPZHKFSQJ-UHFFFAOYSA-N 4-chloro-n-methylpyrimidin-2-amine Chemical compound CNC1=NC=CC(Cl)=N1 UKLSJMPZHKFSQJ-UHFFFAOYSA-N 0.000 description 1
WYLDVMUJJXJBJS-UHFFFAOYSA-N 4-chloro-n-propan-2-ylpyrimidin-2-amine Chemical compound CC(C)NC1=NC=CC(Cl)=N1 WYLDVMUJJXJBJS-UHFFFAOYSA-N 0.000 description 1
NZCRUBBNZGVREM-UHFFFAOYSA-N 4-chlorothieno[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=CS2 NZCRUBBNZGVREM-UHFFFAOYSA-N 0.000 description 1
PVJMCLMUSBVRCI-UHFFFAOYSA-N 4-n-benzyl-6-chloro-2-n,2-n-dimethyl-1,3,5-triazine-2,4-diamine Chemical compound CN(C)C1=NC(Cl)=NC(NCC=2C=CC=CC=2)=N1 PVJMCLMUSBVRCI-UHFFFAOYSA-N 0.000 description 1
COQICWOELDIBCX-UHFFFAOYSA-N 5-benzyl-4-chloro-n,n,6-trimethylpyrimidin-2-amine Chemical compound ClC1=NC(N(C)C)=NC(C)=C1CC1=CC=CC=C1 COQICWOELDIBCX-UHFFFAOYSA-N 0.000 description 1
LSDQYPWZZYCBMH-UHFFFAOYSA-N 5-butyl-4-chloro-n,n,6-trimethylpyrimidin-2-amine Chemical compound CCCCC1=C(C)N=C(N(C)C)N=C1Cl LSDQYPWZZYCBMH-UHFFFAOYSA-N 0.000 description 1
XFUSOCHHDLYPEX-UHFFFAOYSA-N 6-chloro-2-(dimethylamino)-1h-pyrimidin-4-one Chemical compound CN(C)C1=NC(O)=CC(Cl)=N1 XFUSOCHHDLYPEX-UHFFFAOYSA-N 0.000 description 1
TUCAKOVTNXHJDD-UHFFFAOYSA-N 6-chloro-2-n,2-n,4-n-trimethyl-1,3,5-triazine-2,4-diamine Chemical compound CNC1=NC(Cl)=NC(N(C)C)=N1 TUCAKOVTNXHJDD-UHFFFAOYSA-N 0.000 description 1
SIVRBYULLRGOGD-UHFFFAOYSA-N 6-chloro-2-n,2-n-dimethyl-1,3,5-triazine-2,4-diamine Chemical compound CN(C)C1=NC(N)=NC(Cl)=N1 SIVRBYULLRGOGD-UHFFFAOYSA-N 0.000 description 1
JSAYULRNXVSYHK-UHFFFAOYSA-N 6-chloro-2-n,4-n-dimethyl-1,3,5-triazine-2,4-diamine Chemical compound CNC1=NC(Cl)=NC(NC)=N1 JSAYULRNXVSYHK-UHFFFAOYSA-N 0.000 description 1
WAGVAZQFCOMORW-UHFFFAOYSA-N 6-chloro-n,n-dimethylpyrimidin-4-amine Chemical compound CN(C)C1=CC(Cl)=NC=N1 WAGVAZQFCOMORW-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
HJIUPFPIEBPYIE-UHFFFAOYSA-N Crimidine Chemical compound CN(C)C1=CC(C)=NC(Cl)=N1 HJIUPFPIEBPYIE-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000334160 Isatis Species 0.000 description 1
238000002768 Kirby-Bauer method Methods 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000194017 Streptococcus Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
FZRLBTIPZJXREW-UHFFFAOYSA-N ethyl 4-amino-2-chloropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(Cl)N=C1N FZRLBTIPZJXREW-UHFFFAOYSA-N 0.000 description 1
HYYWMBIWYPMBGO-UHFFFAOYSA-N ethyl 4-chloro-2-(dimethylamino)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(N(C)C)N=C1Cl HYYWMBIWYPMBGO-UHFFFAOYSA-N 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
JHKIUAHEOFOQDM-UHFFFAOYSA-N n,n-dibenzyl-2-chloropyrimidin-4-amine Chemical compound ClC1=NC=CC(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=N1 JHKIUAHEOFOQDM-UHFFFAOYSA-N 0.000 description 1
QWRADTLPANSRDT-UHFFFAOYSA-N n-benzyl-2-chloropyrimidin-4-amine Chemical compound ClC1=NC=CC(NCC=2C=CC=CC=2)=N1 QWRADTLPANSRDT-UHFFFAOYSA-N 0.000 description 1
VDDPUCZEHQSAHW-UHFFFAOYSA-N n-benzyl-4-chloropyrimidin-2-amine Chemical compound ClC1=CC=NC(NCC=2C=CC=CC=2)=N1 VDDPUCZEHQSAHW-UHFFFAOYSA-N 0.000 description 1
RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Oncology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Communicable Diseases (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

NO783767A 1977-11-10 1978-11-09 Analogifremgangsmaate for fremstilling av terapeutisk aktive erytromycinderivater NO783767L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772750288 DE2750288A1 (de)	1977-11-10	1977-11-10	Neue 9-(omega-heteroarylamino- alkylamino)-erythromycine, ihre salze, verfahren zu ihrer herstellung und diese enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
NO783767L true NO783767L (no)	1979-05-11

Family

ID=6023435

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO783767A NO783767L (no)	1977-11-10	1978-11-09	Analogifremgangsmaate for fremstilling av terapeutisk aktive erytromycinderivater

Country Status (18)

Country	Link
US (1)	US4256738A (it)
EP (1)	EP0001981B1 (it)
JP (1)	JPS5476588A (it)
AT (1)	AT361623B (it)
AU (1)	AU4144878A (it)
CA (1)	CA1107726A (it)
DE (2)	DE2750288A1 (it)
DK (1)	DK499778A (it)
ES (1)	ES474693A1 (it)
FI (1)	FI783417A7 (it)
GR (1)	GR65281B (it)
IL (1)	IL55906A0 (it)
IT (1)	IT1109331B (it)
NO (1)	NO783767L (it)
NZ (1)	NZ188872A (it)
PT (1)	PT68771A (it)
YU (1)	YU261178A (it)
ZA (1)	ZA786313B (it)

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US5739127A (en) *	1996-11-08	1998-04-14	Bayer Aktiengesellschaft	2,4'-bridged bis-2,4-diaminoquinazolines
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EP1847543A1 (de)	2006-04-19	2007-10-24	Boehringer Ingelheim Pharma GmbH & Co. KG	Dihydrothienopyrimidine zur Behandlung von entzündlichen Erkrankungen
TW200900065A (en)	2007-03-07	2009-01-01	Janssen Pharmaceutica Nv	3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives
TW200845978A (en) *	2007-03-07	2008-12-01	Janssen Pharmaceutica Nv	3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives
SI2203439T1 (sl)	2007-09-14	2011-05-31	Ortho Mcneil Janssen Pharm	1',3'-disubstituirani 4-fenil-3,4,5,6-tetrahidro-2H-1'H-(1,4')bipiridinil-2'-oni
ES2409215T3 (es) *	2007-09-14	2013-06-25	Janssen Pharmaceuticals, Inc.	4-fenil-1H-piridin-2-onas 1-3-disustituidas
BRPI0817101A2 (pt)	2007-09-14	2017-05-09	Addex Pharmaceuticals Sa	4-(aril-x-fenil)-1h-piridin-2-onas 1,3-dissubstituídas
ATE537175T1 (de)	2007-10-19	2011-12-15	Boehringer Ingelheim Int	Neue piperazino-dihydrothienopyrimidin-derivate
ES2524910T3 (es) *	2007-10-19	2014-12-15	Boehringer Ingelheim International Gmbh	Piperidino-dihidrotienopirimidinas sustituidas
JP5341899B2 (ja)	2007-10-19	2013-11-13	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	ヘテロ環置換ピペラジノ−ジヒドロチエノピリミジン
ES2637794T3 (es) *	2007-11-14	2017-10-17	Janssen Pharmaceuticals, Inc.	Derivados de imidazo[1,2-A]piridina y su uso como moduladores alostéricos positivos de receptores MGLUR2
ES2439291T3 (es)	2008-09-02	2014-01-22	Janssen Pharmaceuticals, Inc.	Derivados de 3-azabiciclo[3.1.0]hexilo como moduladores de receptores de glutamato metabotrópicos
CA2738849C (en)	2008-10-16	2016-06-28	Addex Pharma S.A.	Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors
ES2401691T3 (es)	2008-11-28	2013-04-23	Ortho-Mcneil-Janssen Pharmaceuticals, Inc.	Derivados de indol y de benzoxacina como moduladores de los receptores metabotrópicos de glutamato
ES2440001T3 (es)	2009-05-12	2014-01-27	Janssen Pharmaceuticals, Inc.	Derivados de 1,2,4-triazolo[4,3-A]piridina y su uso para el tratamiento o prevención de trastornos neurológicos y psiquiátricos
SG176018A1 (en)	2009-05-12	2011-12-29	Janssen Pharmaceuticals Inc	1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
MY153913A (en)	2009-05-12	2015-04-15	Janssen Pharmaceuticals Inc	7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
ES2552455T3 (es)	2010-11-08	2015-11-30	Janssen Pharmaceuticals, Inc.	Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2
CA2814998C (en)	2010-11-08	2019-10-29	Janssen Pharmaceuticals, Inc.	1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
CN103298809B (zh)	2010-11-08	2016-08-31	杨森制药公司	1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途
US9802954B2 (en)	2011-08-24	2017-10-31	Boehringer Ingelheim International Gmbh	Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma
US20130059866A1 (en)	2011-08-24	2013-03-07	Boehringer Ingelheim International Gmbh	Novel piperidino-dihydrothienopyrimidine sulfoxides and their use for treating copd and asthma
JO3368B1 (ar)	2013-06-04	2019-03-13	Janssen Pharmaceutica Nv	مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2
JO3367B1 (ar)	2013-09-06	2019-03-13	Janssen Pharmaceutica Nv	مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2
KR20160092991A (ko) *	2013-09-27	2016-08-05	님버스 아이리스 인코포레이티드	Irak 억제제 및 이의 용도
US10537573B2 (en)	2014-01-21	2020-01-21	Janssen Pharmaceutica Nv	Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use
IL279202B2 (en)	2014-01-21	2023-09-01	Janssen Pharmaceutica Nv	Combinations containing positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic subtype 2 receptor and their use
CN106674132B (zh) *	2016-11-22	2019-04-26	上海书亚医药科技有限公司	一种嘧啶类除草剂的制备方法与应用
CN112569239B (zh) *	2020-12-18	2021-12-28	北京鑫开元医药科技有限公司	作为tlr8激动剂的药物组合物、其制备方法及其用途

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US3650376A (en) *	1970-08-17	1972-03-21	Conveyor Systems	Accumulating conveyor
GB1345524A (en) *	1970-09-30	1974-01-30	Lilly Industries Ltd	N-heteroarylidene erythomycylamines
DK139522C (da) *	1975-04-07	1979-08-20	Thomae Gmbh Dr K	Analogifremgangsmaade til fremstilling af 9-iminoalkylamino-erythromyciner eller syreadditionssalte deraf
DE2515075C2 (de) *	1975-04-07	1985-10-24	Dr. Karl Thomae Gmbh, 7950 Biberach	Erythromycinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2515077A1 (de) *	1975-04-07	1976-10-28	Thomae Gmbh Dr K	Neue 9-alkylidenamino-erythromycine, ihre salze und verfahren zu ihrer herstellung

1977
- 1977-11-10 DE DE19772750288 patent/DE2750288A1/de not_active Withdrawn
1978
- 1978-10-14 DE DE7878101160T patent/DE2860585D1/de not_active Expired
- 1978-10-14 EP EP78101160A patent/EP0001981B1/de not_active Expired
- 1978-10-30 AT AT773178A patent/AT361623B/de not_active IP Right Cessation
- 1978-10-31 ES ES474693A patent/ES474693A1/es not_active Expired
- 1978-11-03 US US05/957,451 patent/US4256738A/en not_active Expired - Lifetime
- 1978-11-03 GR GR57569A patent/GR65281B/el unknown
- 1978-11-09 JP JP13837278A patent/JPS5476588A/ja active Pending
- 1978-11-09 ZA ZA786313A patent/ZA786313B/xx unknown
- 1978-11-09 YU YU02611/78A patent/YU261178A/xx unknown
- 1978-11-09 AU AU41448/78A patent/AU4144878A/en active Pending
- 1978-11-09 PT PT68771A patent/PT68771A/pt unknown
- 1978-11-09 IT IT51850/78A patent/IT1109331B/it active
- 1978-11-09 IL IL55906A patent/IL55906A0/xx unknown
- 1978-11-09 CA CA316,079A patent/CA1107726A/en not_active Expired
- 1978-11-09 DK DK499778A patent/DK499778A/da unknown
- 1978-11-09 NZ NZ188872A patent/NZ188872A/xx unknown
- 1978-11-09 FI FI783417A patent/FI783417A7/fi unknown
- 1978-11-09 NO NO783767A patent/NO783767L/no unknown

Also Published As

Publication number	Publication date
FI783417A7 (fi)	1979-05-11
US4256738A (en)	1981-03-17
AU4144878A (en)	1979-05-17
DE2750288A1 (de)	1979-05-17
EP0001981A1 (de)	1979-05-30
IT1109331B (it)	1985-12-16
JPS5476588A (en)	1979-06-19
DK499778A (da)	1979-05-11
NZ188872A (en)	1981-05-29
ZA786313B (en)	1980-07-30
CA1107726A (en)	1981-08-25
IT7851850A0 (it)	1978-11-09
AT361623B (de)	1981-03-25
IL55906A0 (en)	1979-01-31
ATA773178A (de)	1980-08-15
EP0001981B1 (de)	1981-04-01
GR65281B (en)	1980-08-01
ES474693A1 (es)	1979-04-01
PT68771A (de)	1978-12-01
YU261178A (en)	1982-08-31
DE2860585D1 (en)	1981-04-23

Publication	Publication Date	Title
NO783767L (no)	1979-05-11	Analogifremgangsmaate for fremstilling av terapeutisk aktive erytromycinderivater
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US10618884B2 (en)	2020-04-14	Deuterated diaminopyrimidine compounds and pharmaceutical compositions comprising such compounds
CN104030990B (zh)	2017-01-04	苯基氨基嘧啶化合物及其用途
US7872020B2 (en)	2011-01-18	TGF-β inhibitors
EP3166608B1 (en)	2018-12-12	Aminopyridazinone compounds as protein kinase inhibitors
AU2004272283B2 (en)	2008-10-02	2,4 di (hetero) -arylamino-pyrimidine derivatives as ZAP-70 and/or Syk inhibitors
WO2006004658A2 (en)	2006-01-12	Furanopyrimidines
EP1915377A1 (en)	2008-04-30	Pyrazolo pyrimidines useful as aurora kinase inhibitors
GB2087881A (en)	1982-06-03	5-substituted methyl-pyrimidine-2,4-diamines
US20210139459A1 (en)	2021-05-13	2h-indazole derivatives as cdk4 and cdk6 inhibitors and therapeutic uses thereof
EP1768984A1 (en)	2007-04-04	Thienopyrimidines useful as aurora kinase inhibitors
US11028097B2 (en)	2021-06-08	Thienopyrimidine compounds
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HK1245771B (en)	2020-09-25	Naphthyridine compounds as jak kinase inhibitors
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