CA2564277A1 - 7h-pyrrolo[2,3-d]pyrimidine derivatives, as well as their therapeutically acceptable salts, pharmaceutical preparations containing them and process for production the active agent - Google Patents
7h-pyrrolo[2,3-d]pyrimidine derivatives, as well as their therapeutically acceptable salts, pharmaceutical preparations containing them and process for production the active agent Download PDFInfo
- Publication number
- CA2564277A1 CA2564277A1 CA002564277A CA2564277A CA2564277A1 CA 2564277 A1 CA2564277 A1 CA 2564277A1 CA 002564277 A CA002564277 A CA 002564277A CA 2564277 A CA2564277 A CA 2564277A CA 2564277 A1 CA2564277 A1 CA 2564277A1
- Authority
- CA
- Canada
- Prior art keywords
- general formula
- pyrrolo
- nmr
- dimethyl
- ppm
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 38
- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 13
- JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical class N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 150000003839 salts Chemical class 0.000 title claims abstract description 8
- 239000013543 active substance Substances 0.000 title abstract description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 230000000202 analgesic effect Effects 0.000 claims abstract description 7
- 230000001741 anti-phlogistic effect Effects 0.000 claims abstract description 7
- 208000004454 Hyperalgesia Diseases 0.000 claims abstract description 6
- 239000002260 anti-inflammatory agent Substances 0.000 claims abstract description 6
- 230000004054 inflammatory process Effects 0.000 claims abstract description 6
- 230000002981 neuropathic effect Effects 0.000 claims abstract description 6
- 208000035154 Hyperesthesia Diseases 0.000 claims abstract description 5
- 210000000988 bone and bone Anatomy 0.000 claims abstract description 5
- 230000006378 damage Effects 0.000 claims abstract description 5
- 241000206576 Chondrus Species 0.000 claims abstract description 4
- 201000004624 Dermatitis Diseases 0.000 claims abstract description 4
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 4
- 208000006673 asthma Diseases 0.000 claims abstract description 4
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 4
- 201000010099 disease Diseases 0.000 claims abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 4
- 201000003068 rheumatic fever Diseases 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 18
- -1 nitro, amino Chemical group 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 9
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 7
- 239000003495 polar organic solvent Substances 0.000 claims description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- 150000002429 hydrazines Chemical class 0.000 claims description 6
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 6
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 239000005457 ice water Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 71
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 8
- 102100024304 Protachykinin-1 Human genes 0.000 description 8
- 101800003906 Substance P Proteins 0.000 description 8
- 229940093499 ethyl acetate Drugs 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- MLDAYAVMTHFOPT-UHFFFAOYSA-N [5,6-dimethyl-7-(3-morpholin-4-ylpropyl)pyrrolo[2,3-d]pyrimidin-4-yl]hydrazine Chemical compound CC1=C(C)C2=C(NN)N=CN=C2N1CCCN1CCOCC1 MLDAYAVMTHFOPT-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 230000005284 excitation Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000003127 radioimmunoassay Methods 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 206010015866 Extravasation Diseases 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 208000007920 Neurogenic Inflammation Diseases 0.000 description 5
- 210000005069 ears Anatomy 0.000 description 5
- 230000036251 extravasation Effects 0.000 description 5
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 4
- ZQMSJWJNYLHMAG-UHFFFAOYSA-N 4-[3-(4-chloro-5,6-dimethylpyrrolo[2,3-d]pyrimidin-7-yl)propyl]morpholine Chemical compound CC1=C(C)C2=C(Cl)N=CN=C2N1CCCN1CCOCC1 ZQMSJWJNYLHMAG-UHFFFAOYSA-N 0.000 description 4
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 4
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 4
- 229960002504 capsaicin Drugs 0.000 description 4
- 229960003699 evans blue Drugs 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000008164 mustard oil Substances 0.000 description 4
- 230000001272 neurogenic effect Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000004526 pharmaceutical effect Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- VKQIQNZNTFXNDV-UHFFFAOYSA-N 4-chloro-n-(3-chlorophenyl)-5,6-dimethylpyrrolo[2,3-d]pyrimidin-7-amine Chemical compound CC1=C(C)C2=C(Cl)N=CN=C2N1NC1=CC=CC(Cl)=C1 VKQIQNZNTFXNDV-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 102000007562 Serum Albumin Human genes 0.000 description 3
- 108010071390 Serum Albumin Proteins 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- ADNPLDHMAVUMIW-CUZNLEPHSA-N substance P Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 ADNPLDHMAVUMIW-CUZNLEPHSA-N 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 210000003437 trachea Anatomy 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KTXPBSHZUNNRIG-UHFFFAOYSA-N 2-amino-1-(3-chloroanilino)-4,5-dimethylpyrrole-3-carbonitrile Chemical compound NC1=C(C#N)C(C)=C(C)N1NC1=CC=CC(Cl)=C1 KTXPBSHZUNNRIG-UHFFFAOYSA-N 0.000 description 2
- PCYGLFXKCBFGPC-UHFFFAOYSA-N 3,4-Dihydroxy hydroxymethyl benzene Natural products OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-UHFFFAOYSA-N 0.000 description 2
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 2
- MBVCESWADCIXJN-UHFFFAOYSA-N 5-Bromoisatin Chemical compound BrC1=CC=C2NC(=O)C(=O)C2=C1 MBVCESWADCIXJN-UHFFFAOYSA-N 0.000 description 2
- XHDJYQWGFIBCEP-UHFFFAOYSA-N 5-Chloro-1H-indole-2,3-dione Chemical compound ClC1=CC=C2NC(=O)C(=O)C2=C1 XHDJYQWGFIBCEP-UHFFFAOYSA-N 0.000 description 2
- ZSUXKRKJJKNFLV-UHFFFAOYSA-N 7-(3-chloroanilino)-5,6-dimethyl-1h-pyrrolo[2,3-d]pyrimidin-4-one Chemical compound CC1=C(C)C(C(N=CN2)=O)=C2N1NC1=CC=CC(Cl)=C1 ZSUXKRKJJKNFLV-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 102000004506 Blood Proteins Human genes 0.000 description 2
- 108010017384 Blood Proteins Proteins 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 240000001307 Myosotis scorpioides Species 0.000 description 2
- 108090000189 Neuropeptides Proteins 0.000 description 2
- 102000003797 Neuropeptides Human genes 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 206010047141 Vasodilatation Diseases 0.000 description 2
- CWCFAVAUWWSGRI-UHFFFAOYSA-N [7-(3-chlorophenyl)-5,6-dimethylpyrrolo[2,3-d]pyrimidin-4-yl]hydrazine Chemical compound CC1=C(C)C2=C(NN)N=CN=C2N1C1=CC=CC(Cl)=C1 CWCFAVAUWWSGRI-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000005638 hydrazono group Chemical group 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229960003299 ketamine Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical class C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 2
- 238000010972 statistical evaluation Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000024883 vasodilation Effects 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 2
- 229960001600 xylazine Drugs 0.000 description 2
- VHWNARFLVWATEW-UHFFFAOYSA-N (7-benzyl-5,6-dimethylpyrrolo[2,3-d]pyrimidin-4-yl)hydrazine Chemical compound CC1=C(C)C2=C(NN)N=CN=C2N1CC1=CC=CC=C1 VHWNARFLVWATEW-UHFFFAOYSA-N 0.000 description 1
- MYRPBJZXSAHNGO-UHFFFAOYSA-N 1,4-dioxane;ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O.C1COCCO1 MYRPBJZXSAHNGO-UHFFFAOYSA-N 0.000 description 1
- KIMSTGGCMQZYGS-UHFFFAOYSA-N 1-hydroxypyrrolo[2,3-d]pyrimidine Chemical compound ON1C=NC=C2C=CN=C12 KIMSTGGCMQZYGS-UHFFFAOYSA-N 0.000 description 1
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
- JJNZXLAFIPKXIG-UHFFFAOYSA-N 2-Chlorobenzylidenemalononitrile Chemical compound ClC1=CC=CC=C1C=C(C#N)C#N JJNZXLAFIPKXIG-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- CGCVHJCZBIYRQC-UHFFFAOYSA-N 4,6-dichloro-1h-indole-2,3-dione Chemical compound ClC1=CC(Cl)=CC2=C1C(=O)C(=O)N2 CGCVHJCZBIYRQC-UHFFFAOYSA-N 0.000 description 1
- KJTRXVXWSSPHRV-UHFFFAOYSA-N 4-benzoyl-5-methyl-2-phenyl-1h-pyrazol-3-one Chemical compound O=C1C(C(=O)C=2C=CC=CC=2)=C(C)NN1C1=CC=CC=C1 KJTRXVXWSSPHRV-UHFFFAOYSA-N 0.000 description 1
- VVFHRCVJCUDXNI-UHFFFAOYSA-N 4-chloro-7-(3-chlorophenyl)-5,6-dimethylpyrrolo[2,3-d]pyrimidine Chemical compound CC1=C(C)C2=C(Cl)N=CN=C2N1C1=CC=CC(Cl)=C1 VVFHRCVJCUDXNI-UHFFFAOYSA-N 0.000 description 1
- YTHJCZRFJGXPTL-UHFFFAOYSA-N 4-hydroxy-3-nitrobenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1[N+]([O-])=O YTHJCZRFJGXPTL-UHFFFAOYSA-N 0.000 description 1
- VAJCSPZKMVQIAP-UHFFFAOYSA-N 5-methyl-1h-indole-2,3-dione Chemical compound CC1=CC=C2NC(=O)C(=O)C2=C1 VAJCSPZKMVQIAP-UHFFFAOYSA-N 0.000 description 1
- MPLXQMMMGDYXIT-UHFFFAOYSA-N 7-chloro-1h-indole-2,3-dione Chemical compound ClC1=CC=CC2=C1NC(=O)C2=O MPLXQMMMGDYXIT-UHFFFAOYSA-N 0.000 description 1
- KTKZSAMDAXOBTG-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidin-2-ylhydrazine Chemical class NNC1=NC=C2C=CNC2=N1 KTKZSAMDAXOBTG-UHFFFAOYSA-N 0.000 description 1
- ISXKAJBUZVKEJP-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidin-4-ylhydrazine Chemical class NNC1=NC=NC2=C1C=CN2 ISXKAJBUZVKEJP-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 208000000114 Pain Threshold Diseases 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 241001456035 Stachys crenata Species 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940043355 kinase inhibitor Drugs 0.000 description 1
- 210000002414 leg Anatomy 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003040 nociceptive effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229940069533 paregoric Drugs 0.000 description 1
- 239000008414 paregoric Substances 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000000816 peptidomimetic Substances 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 238000009521 phase II clinical trial Methods 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- BBBFJLBPOGFECG-UHFFFAOYSA-N salmon calcitonin Chemical compound C=1N=CNC=1CC(C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CCC(N)=O)C(=O)NC(C(C)O)C(=O)NC(CC=1C=CC(O)=CC=1)C(=O)N1C(CCC1)C(=O)NC(CCCNC(N)=N)C(=O)NC(C(C)O)C(=O)NC(CC(N)=O)C(=O)NC(C(C)O)C(=O)NCC(=O)NC(CO)C(=O)NCC(=O)NC(C(C)O)C(=O)N1C(CCC1)C(N)=O)NC(=O)C(CC(C)C)NC(=O)C(CCC(O)=O)NC(=O)C(CCC(N)=O)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(CCCCN)NC(=O)CNC(=O)C(CC(C)C)NC(=O)C(C(C)C)NC(=O)C1CSSCC(N)C(=O)NC(CO)C(=O)NC(CC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(C(C)O)C(=O)N1 BBBFJLBPOGFECG-UHFFFAOYSA-N 0.000 description 1
- 235000008790 seltzer Nutrition 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 210000001258 synovial membrane Anatomy 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0400891A HUP0400891A2 (en) | 2004-04-29 | 2004-04-29 | 7h-pyrrolo[2,3-d]pyrimidine derivatives, their pharmaceutically acceptable salts, pharmaceutical compositions containing them and process for the production of the compounds |
| HUP0400891 | 2004-04-29 | ||
| PCT/HU2005/000040 WO2005105804A1 (en) | 2004-04-29 | 2005-04-25 | 7H-PYRROLO[2,3-d]PYRIMIDINE DERIVATIVES, AS WELL AS THEIR THERAPEUTICALLY ACCEPTABLE SALTS, PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND PROCESS FOR PRODUCTION THE ACTIVE AGENT |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2564277A1 true CA2564277A1 (en) | 2005-11-10 |
Family
ID=89982174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002564277A Abandoned CA2564277A1 (en) | 2004-04-29 | 2005-04-25 | 7h-pyrrolo[2,3-d]pyrimidine derivatives, as well as their therapeutically acceptable salts, pharmaceutical preparations containing them and process for production the active agent |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20080214583A1 (https=) |
| EP (1) | EP1756110B1 (https=) |
| JP (1) | JP2007534737A (https=) |
| KR (1) | KR20070047737A (https=) |
| CN (1) | CN1972946A (https=) |
| AT (1) | ATE462706T1 (https=) |
| AU (1) | AU2005238287A1 (https=) |
| CA (1) | CA2564277A1 (https=) |
| DE (1) | DE602005020281D1 (https=) |
| HU (1) | HUP0400891A2 (https=) |
| IL (1) | IL178906A0 (https=) |
| RU (1) | RU2391344C2 (https=) |
| WO (1) | WO2005105804A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150133426A1 (en) * | 2012-05-21 | 2015-05-14 | Bayer Pharma Aktiengesellschaft | Substituted pyrrolopyrimidines |
| WO2014145576A2 (en) | 2013-03-15 | 2014-09-18 | Northwestern University | Substituted pyrrolo(2,3-d)pyrimidines for the treatment of cancer |
| EP3194399B1 (en) * | 2014-09-17 | 2019-04-10 | Pécsi Tudományegyetem | New agents for treating neurogenic inflammation and neuropathic hyperalgesia related disorders |
| RU2603770C2 (ru) * | 2014-11-28 | 2016-11-27 | Федеральное государственное автономное образовательное учреждение высшего образования "Белгородский государственный национальный исследовательский университет" (НИУ "БелГУ") | Замещенные пиразинопиримидиноны как блокаторы trpa1 каналов, фармацевтическая композиция, способы их получения и применения |
| CN110483526B (zh) * | 2019-09-09 | 2021-10-01 | 辽宁大学 | 含芳基腙结构的吡唑并[1,5-a]嘧啶类衍生物及其应用 |
| CN119613409B (zh) * | 2024-12-05 | 2026-04-17 | 浙江工业大学 | 吡咯并[2,3-d]嘧啶衍生物及其在制备抗炎药物中的应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2818676A1 (de) * | 1978-04-27 | 1979-11-08 | Troponwerke Gmbh & Co Kg | Substituierte 5,6-dimethylpyrrolo 2,3-d pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE69906511T2 (de) * | 1998-05-19 | 2004-01-29 | Otsuka Pharma Co Ltd | PYRAZOLO[1,5-a]PYRIMIDINE |
| RU2001111033A (ru) * | 1998-09-18 | 2003-05-20 | Басф Акциенгезелльшафт (De) | Пирролопиримидины в качестве ингибиторов протеинкиназ |
| EP1382339B1 (en) * | 1999-12-10 | 2007-12-05 | Pfizer Products Inc. | Compositions containing pyrrolo ¬2,3-d pyrimidine derivatives |
| BRPI0514094A (pt) * | 2004-08-02 | 2008-05-27 | Osi Pharm Inc | composto, composição, e, método de tratamento de distúrbio hiperproliferativo |
-
2004
- 2004-04-29 HU HU0400891A patent/HUP0400891A2/hu unknown
-
2005
- 2005-04-25 DE DE602005020281T patent/DE602005020281D1/de not_active Expired - Fee Related
- 2005-04-25 JP JP2007510131A patent/JP2007534737A/ja not_active Withdrawn
- 2005-04-25 CA CA002564277A patent/CA2564277A1/en not_active Abandoned
- 2005-04-25 KR KR1020067025009A patent/KR20070047737A/ko not_active Ceased
- 2005-04-25 AT AT05739554T patent/ATE462706T1/de not_active IP Right Cessation
- 2005-04-25 WO PCT/HU2005/000040 patent/WO2005105804A1/en not_active Ceased
- 2005-04-25 AU AU2005238287A patent/AU2005238287A1/en not_active Abandoned
- 2005-04-25 EP EP05739554A patent/EP1756110B1/en not_active Expired - Lifetime
- 2005-04-25 US US11/587,851 patent/US20080214583A1/en not_active Abandoned
- 2005-04-25 CN CNA2005800206893A patent/CN1972946A/zh active Pending
- 2005-04-25 RU RU2006141393/04A patent/RU2391344C2/ru not_active IP Right Cessation
-
2006
- 2006-10-26 IL IL178906A patent/IL178906A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2005238287A1 (en) | 2005-11-10 |
| HUP0400891A2 (en) | 2006-04-28 |
| US20080214583A1 (en) | 2008-09-04 |
| ATE462706T1 (de) | 2010-04-15 |
| EP1756110B1 (en) | 2010-03-31 |
| RU2391344C2 (ru) | 2010-06-10 |
| WO2005105804A1 (en) | 2005-11-10 |
| HU0400891D0 (en) | 2004-07-28 |
| EP1756110A1 (en) | 2007-02-28 |
| IL178906A0 (en) | 2007-03-08 |
| RU2006141393A (ru) | 2008-06-10 |
| CN1972946A (zh) | 2007-05-30 |
| JP2007534737A (ja) | 2007-11-29 |
| DE602005020281D1 (de) | 2010-05-12 |
| KR20070047737A (ko) | 2007-05-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2213094C2 (ru) | Трициклические соединения, способы их получения, фармацевтическая композиция и способ лечения | |
| AU2017360465B2 (en) | URAT1 inhibitor and use thereof | |
| AU5679096A (en) | Novel deazapurine derivatives; a new class of CRF1 specific ligands | |
| HU193033B (en) | Process for preparing new 6-substituted s-triazolo /3,4-a/ phthalazine derivatives | |
| EP1177195A1 (fr) | 1-AMINO TRIAZOLO 4,3-a! QUINAZOLINE-5-ONES ET/OU -5-THIONES INHIBITRICES DE PHOSPHODIESTERASES IV | |
| WO1999043678A1 (en) | Remedies/preventives for parkinson's disease | |
| TW200837065A (en) | Protein kinase inhibitors | |
| CA2564277A1 (en) | 7h-pyrrolo[2,3-d]pyrimidine derivatives, as well as their therapeutically acceptable salts, pharmaceutical preparations containing them and process for production the active agent | |
| IE910770A1 (en) | "New imidazo [1,2-c] quinazoline derivatives process for preparing these and pharmaceutical compositions containing them" | |
| JPS601171A (ja) | １，２，４−トリアジン誘導体 | |
| Bakhotmah et al. | Synthetic of some new fluorine compounds bearing 1, 2, 4-triazine moieties and the related hetero-polycyclic nitrogen systems as pharmacological probes-overview | |
| HUT50477A (en) | Process for producing tricyclic condensed pyrimidine derivatives and pharmaceutical compositions comprising such compounds | |
| CN110914273B (zh) | 用于治疗糖尿病的作为pde1抑制剂的[1,2,4]三唑并衍生物 | |
| US5358950A (en) | Triazolopyrimidine derivatives which are angiotensin II receptor antagonists | |
| EP0148438A2 (de) | Neue Imidazolderivate, deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| JP6071012B2 (ja) | ４−アミノ−３−フェニルアミノ−６−フェニルピラゾロ［３，４−ｄ］ピリミジン誘導体、その製造および抗ウイルス剤としての使用 | |
| CA2631034A1 (en) | Tricyclic lactam derivatives, their manufacture and use as pharmaceutical agents | |
| HK1106235A (en) | 7h-pyrrolo[2,3-d]pyrimidine derivatives, as well as their therapeutically acceptable salts, pharmaceutical preparations containing them and process for production the active agent | |
| KR100468352B1 (ko) | 신규 피라졸로피리미딘계 유도체, 그의 제조방법 및 이를 유효성분으로 하는 약학적 조성물 | |
| IE902980A1 (en) | Substituted n-heterocyclic groups, the preparation and use¹thereof | |
| MXPA00000758A (es) | Agonistas triciclicos de la vasopresina | |
| CA2028557A1 (en) | Triazolyl hydrazide derivatives and process for their preparation | |
| PL228359B1 (pl) | 1-(1-podstawione-4,5-dihydro-1H-imidazo)-3-chlorosulfonylo pochodne mocznika oraz sposób ich otrzymywania i ich zastosowanie | |
| HK1166075B (en) | Fused pyrimidine-dione derivatives as trpa1 modulators | |
| HK1166075A1 (en) | Fused pyrimidine-dione derivatives as trpa1 modulators |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |