BG107959A - Заместени производни на триазол диамин като киназни инхибитори - Google Patents

Заместени производни на триазол диамин като киназни инхибитори Download PDF

Info

Publication number: BG107959A
Authority: BG; Bulgaria
Prior art keywords: alkyl; group; amino; substituted; independently selected
Prior art date: 2000-12-22

Application number

BG107959A

Other languages

Bulgarian (bg)

English (en)

Inventor

Ronghui Lin

Peter Connolly

Steven Wetter

Shenlin Huang

Stuart Emanual

Robert Guninger

Steven Middleton

Original Assignee

Ortho-Mcneil Pharmaceutical, Inc.

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.)

2000-12-22

Filing date

2003-07-01

Publication date

2004-12-30

2003-07-01 Application filed by Ortho-Mcneil Pharmaceutical, Inc. filed Critical Ortho-Mcneil Pharmaceutical, Inc.

2004-12-30 Publication of BG107959A publication Critical patent/BG107959A/bg

Links

-1 triazole diamine Chemical class 0.000 title claims abstract description 187
229940043355 kinase inhibitor Drugs 0.000 title abstract description 14
239000003757 phosphotransferase inhibitor Substances 0.000 title description 4
108091000080 Phosphotransferase Proteins 0.000 claims abstract description 97
102000020233 phosphotransferase Human genes 0.000 claims abstract description 97
238000000034 method Methods 0.000 claims abstract description 75
230000001404 mediated effect Effects 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims description 624
125000001424 substituent group Chemical group 0.000 claims description 492
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 374
150000001875 compounds Chemical class 0.000 claims description 292
229910052739 hydrogen Inorganic materials 0.000 claims description 273
239000001257 hydrogen Substances 0.000 claims description 270
125000003118 aryl group Chemical group 0.000 claims description 223
125000001072 heteroaryl group Chemical group 0.000 claims description 223
125000000623 heterocyclic group Chemical group 0.000 claims description 201
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 199
125000000753 cycloalkyl group Chemical group 0.000 claims description 168
229910052799 carbon Inorganic materials 0.000 claims description 150
125000004093 cyano group Chemical group *C#N 0.000 claims description 146
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 145
125000001475 halogen functional group Chemical group 0.000 claims description 112
125000004432 carbon atom Chemical group C* 0.000 claims description 105
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 95
125000003545 alkoxy group Chemical group 0.000 claims description 80
125000003342 alkenyl group Chemical group 0.000 claims description 77
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
125000000304 alkynyl group Chemical group 0.000 claims description 51
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 42
150000001335 aliphatic alkanes Chemical class 0.000 claims description 33
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 25
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
239000008194 pharmaceutical composition Substances 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 24
108010034798 CDC2 Protein Kinase Proteins 0.000 claims description 20
102100032857 Cyclin-dependent kinase 1 Human genes 0.000 claims description 20
230000005764 inhibitory process Effects 0.000 claims description 20
125000003282 alkyl amino group Chemical group 0.000 claims description 19
101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims description 17
206010028980 Neoplasm Diseases 0.000 claims description 17
102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims description 17
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
239000002246 antineoplastic agent Substances 0.000 claims description 16
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 16
125000001544 thienyl group Chemical group 0.000 claims description 14
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 12
238000011282 treatment Methods 0.000 claims description 12
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 11
108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 11
229940127089 cytotoxic agent Drugs 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 11
108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims description 10
102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims description 8
102100036252 Cyclin-dependent kinase 4 Human genes 0.000 claims description 8
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 8
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 7
201000011510 cancer Diseases 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000000335 thiazolyl group Chemical group 0.000 claims description 7
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 6
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 6
230000004614 tumor growth Effects 0.000 claims description 6
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
230000001419 dependent effect Effects 0.000 claims description 5
125000002632 imidazolidinyl group Chemical group 0.000 claims description 5
125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 5
125000004193 piperazinyl group Chemical group 0.000 claims description 5
108091008605 VEGF receptors Proteins 0.000 claims description 4
230000033115 angiogenesis Effects 0.000 claims description 4
229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
208000022605 chemotherapy-induced alopecia Diseases 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
230000002829 reductive effect Effects 0.000 claims description 4
208000037803 restenosis Diseases 0.000 claims description 4
125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
206010059245 Angiopathy Diseases 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000005605 benzo group Chemical group 0.000 claims description 3
238000002512 chemotherapy Methods 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000000842 isoxazolyl group Chemical group 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 claims description 2
BDUZYXQIXQZPIL-UHFFFAOYSA-N 1-[4-[[5-amino-1-(3-methylthiophene-2-carbonyl)-1,2,4-triazol-3-yl]amino]phenyl]imidazolidin-2-one Chemical compound C1=CSC(C(=O)N2C(=NC(NC=3C=CC(=CC=3)N3C(NCC3)=O)=N2)N)=C1C BDUZYXQIXQZPIL-UHFFFAOYSA-N 0.000 claims description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
ZUNASHLZAWVKEM-UHFFFAOYSA-N 4-[[5-amino-1-(2-chloro-6-fluoro-3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]benzenesulfonamide Chemical compound CC1=CC=C(F)C(C(=O)N2C(=NC(NC=3C=CC(=CC=3)S(N)(=O)=O)=N2)N)=C1Cl ZUNASHLZAWVKEM-UHFFFAOYSA-N 0.000 claims description 2
108010034265 Vascular Endothelial Growth Factor Receptors Proteins 0.000 claims description 2
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 91
150000002431 hydrogen Chemical group 0.000 claims 50
229940124676 vascular endothelial growth factor receptor Drugs 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
VVGOTCALTHQXFY-UHFFFAOYSA-N 4-[[5-amino-1-(2-chloro-6-fluorobenzoyl)-1,2,4-triazol-3-yl]amino]benzenesulfonamide Chemical compound N=1N(C(=O)C=2C(=CC=CC=2F)Cl)C(N)=NC=1NC1=CC=C(S(N)(=O)=O)C=C1 VVGOTCALTHQXFY-UHFFFAOYSA-N 0.000 claims 1
JBOXDNIWQACYPW-UHFFFAOYSA-N 5-amino-n-(2,6-difluorophenyl)-3-(4-sulfamoylanilino)-1,2,4-triazole-1-carboxamide Chemical compound N=1N(C(=O)NC=2C(=CC=CC=2F)F)C(N)=NC=1NC1=CC=C(S(N)(=O)=O)C=C1 JBOXDNIWQACYPW-UHFFFAOYSA-N 0.000 claims 1
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims 1
101500025419 Homo sapiens Epidermal growth factor Proteins 0.000 claims 1
239000002671 adjuvant Substances 0.000 claims 1
230000005907 cancer growth Effects 0.000 claims 1
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239000003102 growth factor Substances 0.000 claims 1
229940116978 human epidermal growth factor Drugs 0.000 claims 1
GVUGOAYIVIDWIO-UFWWTJHBSA-N nepidermin Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CS)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C(C)C)C(C)C)C1=CC=C(O)C=C1 GVUGOAYIVIDWIO-UFWWTJHBSA-N 0.000 claims 1
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229940127263 dual kinase inhibitor Drugs 0.000 abstract description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 153
238000005481 NMR spectroscopy Methods 0.000 description 149
125000005843 halogen group Chemical group 0.000 description 117
125000002887 hydroxy group Chemical group [H]O* 0.000 description 97
239000011734 sodium Substances 0.000 description 78
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235000020357 syrup Nutrition 0.000 description 1
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230000008685 targeting Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000011285 therapeutic regimen Methods 0.000 description 1
HJZYBDPHAHGHAZ-UHFFFAOYSA-N thiadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSN=N1 HJZYBDPHAHGHAZ-UHFFFAOYSA-N 0.000 description 1
BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 0.000 description 1
125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
WEICZOULVBOQNI-UHFFFAOYSA-N triazole-1,4-diamine;hydrochloride Chemical compound Cl.NC1=CN(N)N=N1 WEICZOULVBOQNI-UHFFFAOYSA-N 0.000 description 1
UXHMGTYELGTNSJ-UHFFFAOYSA-N triazole-1-carboxamide Chemical compound NC(=O)N1C=CN=N1 UXHMGTYELGTNSJ-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical group 0.000 description 1
210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
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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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- 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
- A61K31/4196—1,2,4-Triazoles
- 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
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

BG107959A 2000-12-22 2003-07-01 Заместени производни на триазол диамин като киназни инхибитори BG107959A (bg)

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BG107985A BG107985A (bg)	2000-12-22	2003-07-08	Производни на заместени триазолдиамини, използвани като инхибитори на киназа

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CN (1)	CN100357278C (cs)
AT (1)	ATE328874T1 (cs)
BG (2)	BG107959A (cs)
BR (1)	BR0116792A (cs)
CA (1)	CA2432870A1 (cs)
CZ (1)	CZ20031941A3 (cs)
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DK (1)	DK1355889T3 (cs)
ES (1)	ES2266313T3 (cs)
HU (1)	HUP0303868A3 (cs)
IL (1)	IL156584A0 (cs)
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NZ (1)	NZ526624A (cs)
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WO (1)	WO2002057240A1 (cs)
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2001
- 2001-12-21 MX MXPA03005777A patent/MXPA03005777A/es active IP Right Grant
- 2001-12-21 DE DE60120494T patent/DE60120494T2/de not_active Expired - Lifetime
- 2001-12-21 WO PCT/US2001/050559 patent/WO2002057240A1/en not_active Ceased
- 2001-12-21 ES ES01998116T patent/ES2266313T3/es not_active Expired - Lifetime
- 2001-12-21 IL IL15658401A patent/IL156584A0/xx unknown
- 2001-12-21 CZ CZ20031941A patent/CZ20031941A3/cs unknown
- 2001-12-21 SK SK906-2003A patent/SK9062003A3/sk not_active Application Discontinuation
- 2001-12-21 AT AT01998116T patent/ATE328874T1/de active
- 2001-12-21 PT PT01998116T patent/PT1355889E/pt unknown
- 2001-12-21 NZ NZ526624A patent/NZ526624A/en not_active IP Right Cessation
- 2001-12-21 US US10/029,750 patent/US6924302B2/en not_active Expired - Lifetime
- 2001-12-21 CN CNB018226450A patent/CN100357278C/zh not_active Expired - Fee Related
- 2001-12-21 YU YU51803A patent/YU51803A/sh unknown
- 2001-12-21 BR BR0116792-8A patent/BR0116792A/pt not_active IP Right Cessation
- 2001-12-21 PL PL01363316A patent/PL363316A1/xx not_active Application Discontinuation
- 2001-12-21 RU RU2003118448/04A patent/RU2274639C2/ru not_active IP Right Cessation
- 2001-12-21 DK DK01998116T patent/DK1355889T3/da active
- 2001-12-21 EP EP01998116A patent/EP1355889B1/en not_active Expired - Lifetime
- 2001-12-21 CA CA002432870A patent/CA2432870A1/en not_active Abandoned
- 2001-12-21 HU HU0303868A patent/HUP0303868A3/hu unknown
2003
- 2003-06-20 NO NO20032848A patent/NO20032848L/no not_active Application Discontinuation
- 2003-07-01 BG BG107959A patent/BG107959A/bg unknown
- 2003-07-08 BG BG107985A patent/BG107985A/bg unknown
- 2003-07-21 ZA ZA200305619A patent/ZA200305619B/en unknown
2005
- 2005-02-01 US US11/047,800 patent/US7317031B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US20040077699A1 (en)	2004-04-22
ES2266313T3 (es)	2007-03-01
DK1355889T3 (da)	2006-10-09
YU51803A (sh)	2006-05-25
NO20032848L (no)	2003-08-20
RU2274639C2 (ru)	2006-04-20
SK9062003A3 (en)	2004-04-06
HK1057373A1 (en)	2004-04-02
WO2002057240A1 (en)	2002-07-25
DE60120494T2 (de)	2006-12-21
EP1355889A1 (en)	2003-10-29
PL363316A1 (en)	2004-11-15
CN100357278C (zh)	2007-12-26
US20050182116A1 (en)	2005-08-18
CZ20031941A3 (cs)	2004-08-18
EP1355889B1 (en)	2006-06-07
ATE328874T1 (de)	2006-06-15
RU2003118448A (ru)	2005-01-27
IL156584A0 (en)	2004-01-04
CN1575284A (zh)	2005-02-02
CA2432870A1 (en)	2002-07-25
US7317031B2 (en)	2008-01-08
PT1355889E (pt)	2006-09-29
HUP0303868A3 (en)	2008-03-28
NO20032848D0 (no)	2003-06-20
BG107985A (bg)	2004-11-30
HUP0303868A2 (hu)	2004-03-01
DE60120494D1 (de)	2006-07-20
BR0116792A (pt)	2004-02-17
ZA200305619B (en)	2004-10-21
MXPA03005777A (es)	2005-02-14
NZ526624A (en)	2005-07-29
US6924302B2 (en)	2005-08-02

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