IL221829A - Heterocyclic inhibitors of histamine receptors for the treatment of the disease - Google Patents
Heterocyclic inhibitors of histamine receptors for the treatment of the diseaseInfo
- Publication number
- IL221829A IL221829A IL221829A IL22182912A IL221829A IL 221829 A IL221829 A IL 221829A IL 221829 A IL221829 A IL 221829A IL 22182912 A IL22182912 A IL 22182912A IL 221829 A IL221829 A IL 221829A
- Authority
- IL
- Israel
- Prior art keywords
- chosen
- recited
- compound
- amino
- optionally substituted
- Prior art date
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims 5
- 201000010099 disease Diseases 0.000 title claims 3
- 102000000543 Histamine Receptors Human genes 0.000 title 1
- 108010002059 Histamine Receptors Proteins 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000001424 substituent group Chemical group 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 125000001188 haloalkyl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 12
- -1 amino, hydroxy Chemical group 0.000 claims 11
- 125000002950 monocyclic group Chemical group 0.000 claims 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 5
- 229930192474 thiophene Natural products 0.000 claims 5
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 4
- 239000005557 antagonist Substances 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 3
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 208000010668 atopic eczema Diseases 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 3
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 3
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 3
- 150000003852 triazoles Chemical class 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 2
- 208000003251 Pruritus Diseases 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 230000000172 allergic effect Effects 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 239000003246 corticosteroid Substances 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- ZKLPARSLTMPFCP-OAQYLSRUSA-N 2-[2-[4-[(R)-(4-chlorophenyl)-phenylmethyl]-1-piperazinyl]ethoxy]acetic acid Chemical compound C1CN(CCOCC(=O)O)CCN1[C@@H](C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-OAQYLSRUSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- MBUVEWMHONZEQD-UHFFFAOYSA-N Azeptin Chemical compound C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 MBUVEWMHONZEQD-UHFFFAOYSA-N 0.000 claims 1
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims 1
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims 1
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 1
- 206010013774 Dry eye Diseases 0.000 claims 1
- 206010018258 Giant papillary conjunctivitis Diseases 0.000 claims 1
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 claims 1
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 claims 1
- PVLJETXTTWAYEW-UHFFFAOYSA-N Mizolastine Chemical compound N=1C=CC(=O)NC=1N(C)C(CC1)CCN1C1=NC2=CC=CC=C2N1CC1=CC=C(F)C=C1 PVLJETXTTWAYEW-UHFFFAOYSA-N 0.000 claims 1
- 206010028735 Nasal congestion Diseases 0.000 claims 1
- 206010028741 Nasal inflammation Diseases 0.000 claims 1
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 claims 1
- 208000022873 Ocular disease Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010040742 Sinus congestion Diseases 0.000 claims 1
- 229960003792 acrivastine Drugs 0.000 claims 1
- PWACSDKDOHSSQD-IUTFFREVSA-N acrivastine Chemical compound C1=CC(C)=CC=C1C(\C=1N=C(\C=C\C(O)=O)C=CC=1)=C/CN1CCCC1 PWACSDKDOHSSQD-IUTFFREVSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 229960001919 alcaftadine Drugs 0.000 claims 1
- MWTBKTRZPHJQLH-UHFFFAOYSA-N alcaftadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CCN2C(C=O)=CN=C21 MWTBKTRZPHJQLH-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 229960002469 antazoline Drugs 0.000 claims 1
- REYFJDPCWQRWAA-UHFFFAOYSA-N antazoline Chemical compound N=1CCNC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 REYFJDPCWQRWAA-UHFFFAOYSA-N 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 229960004574 azelastine Drugs 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 229940092705 beclomethasone Drugs 0.000 claims 1
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 claims 1
- 229960003166 bromazine Drugs 0.000 claims 1
- ZQDJSWUEGOYDGT-UHFFFAOYSA-N bromazine hydrochloride Chemical compound [Cl-].C=1C=C(Br)C=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 ZQDJSWUEGOYDGT-UHFFFAOYSA-N 0.000 claims 1
- 229960000725 brompheniramine Drugs 0.000 claims 1
- ZDIGNSYAACHWNL-UHFFFAOYSA-N brompheniramine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Br)C=C1 ZDIGNSYAACHWNL-UHFFFAOYSA-N 0.000 claims 1
- 229960004436 budesonide Drugs 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229960001803 cetirizine Drugs 0.000 claims 1
- 229960003291 chlorphenamine Drugs 0.000 claims 1
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 claims 1
- 229960003728 ciclesonide Drugs 0.000 claims 1
- 229960002881 clemastine Drugs 0.000 claims 1
- YNNUSGIPVFPVBX-NHCUHLMSSA-N clemastine Chemical compound CN1CCC[C@@H]1CCO[C@@](C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-NHCUHLMSSA-N 0.000 claims 1
- 229960000520 diphenhydramine Drugs 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- 229960000879 diphenylpyraline Drugs 0.000 claims 1
- OWQUZNMMYNAXSL-UHFFFAOYSA-N diphenylpyraline Chemical compound C1CN(C)CCC1OC(C=1C=CC=CC=1)C1=CC=CC=C1 OWQUZNMMYNAXSL-UHFFFAOYSA-N 0.000 claims 1
- 229960001971 ebastine Drugs 0.000 claims 1
- MJJALKDDGIKVBE-UHFFFAOYSA-N ebastine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)CCCN1CCC(OC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 MJJALKDDGIKVBE-UHFFFAOYSA-N 0.000 claims 1
- 229960000325 emedastine Drugs 0.000 claims 1
- KBUZBQVCBVDWKX-UHFFFAOYSA-N emedastine Chemical compound N=1C2=CC=CC=C2N(CCOCC)C=1N1CCCN(C)CC1 KBUZBQVCBVDWKX-UHFFFAOYSA-N 0.000 claims 1
- 229960003449 epinastine Drugs 0.000 claims 1
- WHWZLSFABNNENI-UHFFFAOYSA-N epinastine Chemical compound C1C2=CC=CC=C2C2CN=C(N)N2C2=CC=CC=C21 WHWZLSFABNNENI-UHFFFAOYSA-N 0.000 claims 1
- 229960003592 fexofenadine Drugs 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 229960002714 fluticasone Drugs 0.000 claims 1
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 229960000930 hydroxyzine Drugs 0.000 claims 1
- ZQDWXGKKHFNSQK-UHFFFAOYSA-N hydroxyzine Chemical compound C1CN(CCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZQDWXGKKHFNSQK-UHFFFAOYSA-N 0.000 claims 1
- 229960004958 ketotifen Drugs 0.000 claims 1
- 229960001120 levocabastine Drugs 0.000 claims 1
- ZCGOMHNNNFPNMX-KYTRFIICSA-N levocabastine Chemical compound C1([C@@]2(C(O)=O)CCN(C[C@H]2C)[C@@H]2CC[C@@](CC2)(C#N)C=2C=CC(F)=CC=2)=CC=CC=C1 ZCGOMHNNNFPNMX-KYTRFIICSA-N 0.000 claims 1
- 229960001508 levocetirizine Drugs 0.000 claims 1
- 229960003088 loratadine Drugs 0.000 claims 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960004056 methdilazine Drugs 0.000 claims 1
- HTMIBDQKFHUPSX-UHFFFAOYSA-N methdilazine Chemical compound C1N(C)CCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 HTMIBDQKFHUPSX-UHFFFAOYSA-N 0.000 claims 1
- 229960001144 mizolastine Drugs 0.000 claims 1
- 229960001664 mometasone Drugs 0.000 claims 1
- QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 claims 1
- 208000037916 non-allergic rhinitis Diseases 0.000 claims 1
- 229960004114 olopatadine Drugs 0.000 claims 1
- JBIMVDZLSHOPLA-LSCVHKIXSA-N olopatadine Chemical compound C1OC2=CC=C(CC(O)=O)C=C2C(=C/CCN(C)C)\C2=CC=CC=C21 JBIMVDZLSHOPLA-LSCVHKIXSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229960003910 promethazine Drugs 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 229960001128 triprolidine Drugs 0.000 claims 1
- CBEQULMOCCWAQT-WOJGMQOQSA-N triprolidine Chemical compound C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C/CN1CCCC1 CBEQULMOCCWAQT-WOJGMQOQSA-N 0.000 claims 1
- 201000005539 vernal conjunctivitis Diseases 0.000 claims 1
- 208000018464 vernal keratoconjunctivitis Diseases 0.000 claims 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
-
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P17/04—Antipruritics
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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
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- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
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- Dermatology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31261510P | 2010-03-10 | 2010-03-10 | |
| PCT/US2011/027817 WO2011112766A2 (en) | 2010-03-10 | 2011-03-10 | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL221829A true IL221829A (en) | 2014-11-30 |
Family
ID=44564108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL221829A IL221829A (en) | 2010-03-10 | 2012-09-06 | Heterocyclic inhibitors of histamine receptors for the treatment of the disease |
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| EP (1) | EP2545058B1 (enExample) |
| JP (1) | JP5888654B2 (enExample) |
| KR (1) | KR20130016253A (enExample) |
| CN (1) | CN102869666B (enExample) |
| AR (1) | AR080496A1 (enExample) |
| AU (1) | AU2011224316B2 (enExample) |
| BR (1) | BR112012022211A2 (enExample) |
| CA (1) | CA2791417A1 (enExample) |
| ES (1) | ES2607125T3 (enExample) |
| IL (1) | IL221829A (enExample) |
| MX (1) | MX2012010404A (enExample) |
| NZ (1) | NZ602041A (enExample) |
| PH (1) | PH12012501783A1 (enExample) |
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| TW (1) | TW201200518A (enExample) |
| UY (1) | UY33271A (enExample) |
| WO (1) | WO2011112766A2 (enExample) |
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| US8859550B2 (en) * | 2011-09-12 | 2014-10-14 | Kalypsys, Inc. | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
| US9266891B2 (en) | 2012-11-16 | 2016-02-23 | Boehringer Ingelheim International Gmbh | Substituted [1,2,4]triazolo[4,3-A]pyrazines that are BRD4 inhibitors |
| NZ712949A (en) | 2013-05-02 | 2017-04-28 | Pfizer | Imidazo-triazine derivatives as pde10 inhibitors |
| PE20161065A1 (es) | 2013-10-18 | 2016-11-19 | Celgene Quanticel Res Inc | Inhibidores de bromodominio |
| DK3105226T3 (da) | 2014-02-13 | 2019-10-14 | Incyte Corp | Cyclopropylaminer som lsd1-inhibitorer |
| PT3105218T (pt) | 2014-02-13 | 2019-12-05 | Incyte Corp | Ciclopropilaminas como inibidores de lsd1 |
| EP3105219B9 (en) | 2014-02-13 | 2018-10-03 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| US9758523B2 (en) | 2014-07-10 | 2017-09-12 | Incyte Corporation | Triazolopyridines and triazolopyrazines as LSD1 inhibitors |
| TW201613925A (en) | 2014-07-10 | 2016-04-16 | Incyte Corp | Imidazopyrazines as LSD1 inhibitors |
| TWI687419B (zh) | 2014-07-10 | 2020-03-11 | 美商英塞特公司 | 作為ｌｓｄ１抑制劑之咪唑并吡啶及咪唑并吡嗪 |
| TW201625635A (zh) | 2014-11-21 | 2016-07-16 | 默沙東藥廠 | 作為可溶性鳥苷酸環化酶活化劑之三唑并吡基衍生物 |
| ES2722048T3 (es) | 2014-12-23 | 2019-08-07 | Novartis Ag | Compuestos de triazolopirimidina y usos de los mismos |
| EP3626720A1 (en) | 2015-04-03 | 2020-03-25 | Incyte Corporation | Heterocyclic compounds as lsd1 inhibitors |
| KR102710120B1 (ko) | 2015-08-12 | 2024-09-27 | 인사이트 홀딩스 코포레이션 | Lsd1 저해제의 염 |
| PE20190377A1 (es) | 2016-04-22 | 2019-03-08 | Incyte Corp | Formulaciones de un inhibidor de lsd 1 |
| EP3472161B1 (en) | 2016-06-20 | 2020-03-25 | Novartis AG | Triazolopyridine compounds and uses thereof |
| US11091489B2 (en) | 2016-06-20 | 2021-08-17 | Novartis Ag | Crystalline forms of a triazolopyrimidine compound |
| EP3472166A1 (en) | 2016-06-20 | 2019-04-24 | Novartis AG | Imidazopyrimidine compounds useful for the treatment of cancer |
| EP3568395A1 (de) | 2017-01-10 | 2019-11-20 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
| US11058115B2 (en) | 2017-01-10 | 2021-07-13 | Bayer Aktiengesellschaft | Heterocycle derivatives as pesticides |
| SG11201906209SA (en) | 2017-01-23 | 2019-08-27 | Revolution Medicines Inc | Bicyclic compounds as allosteric shp2 inhibitors |
| TW201920150A (zh) | 2017-08-01 | 2019-06-01 | 美商施萬生物製藥研發 Ip有限責任公司 | 作為jak激酶抑制劑之吡唑并及三唑并雙環化合物 |
| JP2020536881A (ja) * | 2017-10-12 | 2020-12-17 | レヴォリューション・メディスンズ，インコーポレイテッド | アロステリックｓｈｐ２阻害剤としてのピリジン、ピラジンおよびトリアジン化合物 |
| RU2020123241A (ru) * | 2017-12-15 | 2022-01-17 | Революшн Медсинз, Инк. | Полициклические соединения в качестве аллостерических ингибиторов shp2 |
| CN115448923B (zh) * | 2018-02-13 | 2024-03-22 | 上海青煜医药科技有限公司 | 嘧啶并环化合物及其制备方法和应用 |
| US11498930B2 (en) | 2018-02-13 | 2022-11-15 | Blueray Therapeutics (Shanghai) Co., Ltd | Pyrimidine-fused cyclic compound, preparation method therefor and application thereof |
| CN110655520A (zh) * | 2018-06-29 | 2020-01-07 | 上海青煜医药科技有限公司 | 嘧啶并环化合物及其制备方法和应用 |
| MA52422A (fr) | 2018-02-27 | 2021-01-06 | Incyte Corp | Imidazopyrimidines et triazolopyrimidines en tant qu'inhibiteurs a2a/a2b |
| MX2020012376A (es) | 2018-05-18 | 2021-03-09 | Incyte Corp | Derivados de pirimidina fusionados como inhibidores de los receptores de adenosina a2a/a2b. |
| MA53097A (fr) | 2018-07-05 | 2021-05-12 | Incyte Corp | Dérivés de pyrazine fusionnés en tant qu'inhibiteurs d'a2a/a2b |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
| TW202028207A (zh) | 2018-09-25 | 2020-08-01 | 美商英塞特公司 | 吡唑并嘧啶化合物及其用途 |
| US12281118B2 (en) | 2018-11-07 | 2025-04-22 | Shanghai Ringene Biopharma Co., Ltd. | Nitrogen-containing fused heterocyclic SHP2 inhibitor compound, preparation method, and use |
| CN113272303B (zh) * | 2018-11-30 | 2024-09-17 | 上海拓界生物医药科技有限公司 | 嘧啶并五元氮杂环类衍生物、其制备方法及其在医药上的应用 |
| CN113498352A (zh) | 2019-01-23 | 2021-10-12 | 施万生物制药研发Ip有限责任公司 | 作为jak抑制剂的咪唑并[1,5-a]吡啶、1,2,4-三唑并[4,3-a]吡啶和咪唑并[1,5-a]吡嗪 |
| TWI829857B (zh) | 2019-01-29 | 2024-01-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶 |
| CN112409385B (zh) * | 2019-08-22 | 2024-08-13 | 上海青煜医药科技有限公司 | 氮杂芳基化合物及其应用 |
| JP2024540574A (ja) * | 2021-11-19 | 2024-10-31 | クロシグナル セラピューティクス，インコーポレイテッド | アデノシン受容体拮抗薬 |
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| US3929812A (en) * | 1974-05-20 | 1975-12-30 | Squibb & Sons Inc | Derivatives of 1H-triazolo {8 4,5-c{9 pyridine-7-carboxylic acids and esters |
| DE4337611A1 (de) * | 1993-11-04 | 1995-05-11 | Boehringer Ingelheim Kg | Neue Benzoylguanidine, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| EP1430898A4 (en) * | 2001-09-28 | 2005-11-02 | Kyowa Hakko Kogyo Kk | Receptor antagonist |
| US6921762B2 (en) * | 2001-11-16 | 2005-07-26 | Amgen Inc. | Substituted indolizine-like compounds and methods of use |
| EP1533312A4 (en) * | 2002-06-25 | 2006-05-31 | Kyowa Hakko Kogyo Kk | HETEROBICYCLIC COMPOUNDS |
| UA79309C2 (en) | 2002-09-06 | 2007-06-11 | Janssen Pharmaceutica Nv | Heterocyclic compounds |
| WO2005121140A1 (en) * | 2004-06-09 | 2005-12-22 | Glaxo Group Limited | Pyrrolopyridine derivatives |
| US20090182140A1 (en) * | 2005-12-02 | 2009-07-16 | Mitsubishi Tanabe Pharma Corporation | Alicyclic Heterocyclic Compound |
| US7807671B2 (en) * | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
| BRPI0712531A2 (pt) * | 2006-05-31 | 2012-12-25 | Galapagos Nv | composto de triazolopirazina éteis para o tratamento de doenÇas degenarativas e inflamatàrias |
| US20100016293A1 (en) * | 2006-07-03 | 2010-01-21 | Rogier Adriaan Smits | Quinazolines and Related Heterocyclic Compounds, and Their Therapeutic Use |
| EP2066645A2 (en) | 2006-09-12 | 2009-06-10 | UCB Pharma S.A. | 2 amino-pyrimidine derivatives as h4 receptor antagonists, processes for preparing them and their use in pharmaceutical compositions |
| US8952160B2 (en) * | 2008-01-11 | 2015-02-10 | Fibrogen, Inc. | Isothiazole-pyridine derivatives as modulators of HIF (hypoxia inducible factor) activity |
| PL2247294T3 (pl) | 2008-02-08 | 2014-09-30 | Basilea Pharmaceutica Ag | Makrolidy do leczenia chorób przez hamowanie PDE |
| KR20110095857A (ko) | 2008-09-10 | 2011-08-25 | 칼립시스, 인코포레이티드 | 질환의 치료를 위한 히스타민 수용체의 헤테로시클릭 억제제 |
| AU2009291783A1 (en) * | 2008-09-10 | 2010-03-18 | Alcon Research, Ltd | Aminopyrimidine inhibitors of histamine receptors for the treatment of disease |
| CN102428087B (zh) * | 2009-04-16 | 2015-06-17 | 卡洛斯三世国家癌症研究中心基金会 | 用作激酶抑制剂的咪唑并吡嗪类化合物 |
| EP2464647B1 (en) * | 2009-08-11 | 2016-09-21 | Bristol-Myers Squibb Company | Azaindazoles as btk kinase modulators and use thereof |
| RS58691B1 (sr) | 2009-12-17 | 2019-06-28 | Merial Inc | Antiparazitske kompozicije dihidroazola |
| EP2526102B1 (en) | 2010-01-22 | 2017-03-08 | Fundación Centro Nacional de Investigaciones Oncológicas Carlos III | Inhibitors of PI3 kinase |
| US20110190269A1 (en) * | 2010-02-01 | 2011-08-04 | Karlheinz Baumann | Gamma secretase modulators |
| WO2011112687A2 (en) | 2010-03-10 | 2011-09-15 | Kalypsys, Inc. | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
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2011
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- 2011-03-10 WO PCT/US2011/027817 patent/WO2011112766A2/en not_active Ceased
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- 2011-03-10 AU AU2011224316A patent/AU2011224316B2/en not_active Ceased
- 2011-03-10 UY UY0001033271A patent/UY33271A/es not_active Application Discontinuation
- 2011-03-10 RU RU2012137180/04A patent/RU2012137180A/ru not_active Application Discontinuation
- 2011-03-10 CN CN201180019492.3A patent/CN102869666B/zh not_active Expired - Fee Related
- 2011-03-10 US US13/044,661 patent/US8569300B2/en not_active Expired - Fee Related
- 2011-03-10 KR KR1020127026253A patent/KR20130016253A/ko not_active Withdrawn
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- 2011-03-10 PH PH1/2012/501783A patent/PH12012501783A1/en unknown
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- 2011-03-10 JP JP2012557231A patent/JP5888654B2/ja not_active Expired - Fee Related
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2012
- 2012-09-06 IL IL221829A patent/IL221829A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP5888654B2 (ja) | 2016-03-22 |
| EP2545058A4 (en) | 2013-07-24 |
| WO2011112766A3 (en) | 2012-01-19 |
| ES2607125T3 (es) | 2017-03-29 |
| TW201200518A (en) | 2012-01-01 |
| EP2545058B1 (en) | 2016-08-24 |
| MX2012010404A (es) | 2013-05-20 |
| US8569300B2 (en) | 2013-10-29 |
| CA2791417A1 (en) | 2011-09-15 |
| AU2011224316A1 (en) | 2012-09-13 |
| JP2013522222A (ja) | 2013-06-13 |
| CN102869666A (zh) | 2013-01-09 |
| AU2011224316B2 (en) | 2016-09-15 |
| BR112012022211A2 (pt) | 2017-07-18 |
| PH12012501783A1 (en) | 2015-06-26 |
| RU2012137180A (ru) | 2014-04-20 |
| AR080496A1 (es) | 2012-04-11 |
| WO2011112766A2 (en) | 2011-09-15 |
| UY33271A (es) | 2011-10-31 |
| KR20130016253A (ko) | 2013-02-14 |
| NZ602041A (en) | 2014-08-29 |
| US20110237565A1 (en) | 2011-09-29 |
| CN102869666B (zh) | 2015-09-09 |
| EP2545058A2 (en) | 2013-01-16 |
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