NO317301B1 - N-(3-etynylfenylamino)-6,7-bis(2-metoksyetoksy)-4-quinazolinamin mesylat anhydrat og monohydrat - Google Patents

N-(3-etynylfenylamino)-6,7-bis(2-metoksyetoksy)-4-quinazolinamin mesylat anhydrat og monohydrat Download PDF

Info

Publication number: NO317301B1
Authority: NO; Norway
Prior art keywords: compound; polymorph; pharmaceutical composition; bis; methoxyethoxy
Prior art date: 1998-04-29

Application number

NO20005453A

Other languages

English (en)

Norwegian (no)

Other versions

NO20005453D0 (no

NO20005453L (no

Inventor

Jeffrey William Raggon

Ravi Mysore Shanker

Dinos Paul Santafianos

Douglas John Meldrum Allen

Timothy Norris

Original Assignee

Osi Pharm 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.)

1998-04-29

Filing date

2000-10-27

Publication date

2004-10-04

2000-10-27 Application filed by Osi Pharm Inc filed Critical Osi Pharm Inc

2000-10-27 Publication of NO20005453D0 publication Critical patent/NO20005453D0/no

2000-12-20 Publication of NO20005453L publication Critical patent/NO20005453L/no

2004-10-04 Publication of NO317301B1 publication Critical patent/NO317301B1/no

Links

150000004682 monohydrates Chemical class 0.000 title description 8
ZKHFAIQCKLXUHC-UHFFFAOYSA-N 1-[6,7-bis(2-methoxyethoxy)quinazolin-4-yl]-2-(3-ethynylphenyl)hydrazine;methanesulfonic acid Chemical compound CS(O)(=O)=O.C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NNC1=CC=CC(C#C)=C1 ZKHFAIQCKLXUHC-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 44
239000008194 pharmaceutical composition Substances 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
206010028980 Neoplasm Diseases 0.000 claims description 17
PCBNMUVSOAYYIH-UHFFFAOYSA-N n-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 PCBNMUVSOAYYIH-UHFFFAOYSA-N 0.000 claims description 13
238000000634 powder X-ray diffraction Methods 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 12
241000124008 Mammalia Species 0.000 claims description 11
230000003463 hyperproliferative effect Effects 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 9
239000003112 inhibitor Substances 0.000 claims description 9
201000011510 cancer Diseases 0.000 claims description 8
238000002156 mixing Methods 0.000 claims description 8
210000002307 prostate Anatomy 0.000 claims description 8
210000000481 breast Anatomy 0.000 claims description 6
210000003734 kidney Anatomy 0.000 claims description 6
210000004072 lung Anatomy 0.000 claims description 6
210000004027 cell Anatomy 0.000 claims description 5
208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
230000000340 anti-metabolite Effects 0.000 claims description 4
229940100197 antimetabolite Drugs 0.000 claims description 4
239000002256 antimetabolite Substances 0.000 claims description 4
210000004556 brain Anatomy 0.000 claims description 4
230000002611 ovarian Effects 0.000 claims description 4
210000000496 pancreas Anatomy 0.000 claims description 4
210000002784 stomach Anatomy 0.000 claims description 4
210000003932 urinary bladder Anatomy 0.000 claims description 4
229940123587 Cell cycle inhibitor Drugs 0.000 claims description 3
102000004190 Enzymes Human genes 0.000 claims description 3
108090000790 Enzymes Proteins 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
239000003242 anti bacterial agent Substances 0.000 claims description 3
230000002280 anti-androgenic effect Effects 0.000 claims description 3
230000003388 anti-hormonal effect Effects 0.000 claims description 3
239000000051 antiandrogen Substances 0.000 claims description 3
229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 claims description 3
229940088710 antibiotic agent Drugs 0.000 claims description 3
239000002246 antineoplastic agent Substances 0.000 claims description 3
239000003102 growth factor Substances 0.000 claims description 3
230000000394 mitotic effect Effects 0.000 claims description 3
PSJLNUIGIVWKGK-UHFFFAOYSA-N n-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine;methanesulfonic acid;hydrate Chemical compound O.CS(O)(=O)=O.C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 PSJLNUIGIVWKGK-UHFFFAOYSA-N 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 3
239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
229940088598 enzyme Drugs 0.000 claims description 2
239000000367 immunologic factor Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
210000001672 ovary Anatomy 0.000 claims description 2
210000000664 rectum Anatomy 0.000 claims description 2
201000002510 thyroid cancer Diseases 0.000 claims description 2
229940044693 topoisomerase inhibitor Drugs 0.000 claims description 2
210000003128 head Anatomy 0.000 claims 2
210000003739 neck Anatomy 0.000 claims 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
239000000203 mixture Substances 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
208000035475 disorder Diseases 0.000 description 12
238000000034 method Methods 0.000 description 12
239000000243 solution Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 11
239000000047 product Substances 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000002002 slurry Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
108060006698 EGF receptor Proteins 0.000 description 8
102000001301 EGF receptor Human genes 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
206010004446 Benign prostatic hyperplasia Diseases 0.000 description 7
208000004403 Prostatic Hyperplasia Diseases 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
GTTBEUCJPZQMDZ-UHFFFAOYSA-N erlotinib hydrochloride Chemical compound [H+].[Cl-].C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 GTTBEUCJPZQMDZ-UHFFFAOYSA-N 0.000 description 6
229940098779 methanesulfonic acid Drugs 0.000 description 6
102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 5
108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 5
201000004681 Psoriasis Diseases 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
238000002441 X-ray diffraction Methods 0.000 description 4
239000002250 absorbent Substances 0.000 description 4
230000002745 absorbent Effects 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000000758 substrate Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
102100033237 Pro-epidermal growth factor Human genes 0.000 description 3
101710098940 Pro-epidermal growth factor Proteins 0.000 description 3
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 3
238000013019 agitation Methods 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
-1 hydrochloride compound Chemical class 0.000 description 3
206010020718 hyperplasia Diseases 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
OIXMUQLVDNPHNS-UHFFFAOYSA-N methanesulfonic acid;hydrate Chemical compound O.CS(O)(=O)=O OIXMUQLVDNPHNS-UHFFFAOYSA-N 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
238000006366 phosphorylation reaction Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
201000009030 Carcinoma Diseases 0.000 description 2
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
206010018338 Glioma Diseases 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
238000004497 NIR spectroscopy Methods 0.000 description 2
206010039491 Sarcoma Diseases 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000001594 aberrant effect Effects 0.000 description 2
230000004913 activation Effects 0.000 description 2
230000033115 angiogenesis Effects 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
201000010099 disease Diseases 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
230000014509 gene expression Effects 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
208000017169 kidney disease Diseases 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
201000001441 melanoma Diseases 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000012544 monitoring process Methods 0.000 description 2
231100000590 oncogenic Toxicity 0.000 description 2
230000002246 oncogenic effect Effects 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000026731 phosphorylation Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
230000004862 vasculogenesis Effects 0.000 description 2
VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
GMDWHBVEZCVCHU-UHFFFAOYSA-N 2-(2-methoxyethoxy)quinazolin-4-amine Chemical compound C1=CC=CC2=NC(OCCOC)=NC(N)=C21 GMDWHBVEZCVCHU-UHFFFAOYSA-N 0.000 description 1
241000220479 Acacia Species 0.000 description 1
206010000830 Acute leukaemia Diseases 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
108010006654 Bleomycin Proteins 0.000 description 1
206010005949 Bone cancer Diseases 0.000 description 1
208000018084 Bone neoplasm Diseases 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
206010007953 Central nervous system lymphoma Diseases 0.000 description 1
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
206010012689 Diabetic retinopathy Diseases 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
206010014733 Endometrial cancer Diseases 0.000 description 1
206010014759 Endometrial neoplasm Diseases 0.000 description 1
208000009849 Female Genital Neoplasms Diseases 0.000 description 1
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
201000003741 Gastrointestinal carcinoma Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
208000032612 Glial tumor Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000007995 HEPES buffer Substances 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
208000017604 Hodgkin disease Diseases 0.000 description 1
208000010747 Hodgkins lymphoma Diseases 0.000 description 1
101000851176 Homo sapiens Pro-epidermal growth factor Proteins 0.000 description 1
102000014150 Interferons Human genes 0.000 description 1
108010050904 Interferons Proteins 0.000 description 1
206010061252 Intraocular melanoma Diseases 0.000 description 1
208000007766 Kaposi sarcoma Diseases 0.000 description 1
208000008839 Kidney Neoplasms Diseases 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
206010025323 Lymphomas Diseases 0.000 description 1
208000032271 Malignant tumor of penis Diseases 0.000 description 1
241001077660 Molo Species 0.000 description 1
LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 description 1
206010061535 Ovarian neoplasm Diseases 0.000 description 1
206010061902 Pancreatic neoplasm Diseases 0.000 description 1
206010033645 Pancreatitis Diseases 0.000 description 1
208000002471 Penile Neoplasms Diseases 0.000 description 1
206010034299 Penile cancer Diseases 0.000 description 1
208000007913 Pituitary Neoplasms Diseases 0.000 description 1
206010060862 Prostate cancer Diseases 0.000 description 1
208000000236 Prostatic Neoplasms Diseases 0.000 description 1
230000010799 Receptor Interactions Effects 0.000 description 1
101710100969 Receptor tyrosine-protein kinase erbB-3 Proteins 0.000 description 1
102100029986 Receptor tyrosine-protein kinase erbB-3 Human genes 0.000 description 1
102100029981 Receptor tyrosine-protein kinase erbB-4 Human genes 0.000 description 1
101710100963 Receptor tyrosine-protein kinase erbB-4 Proteins 0.000 description 1
208000015634 Rectal Neoplasms Diseases 0.000 description 1
208000006265 Renal cell carcinoma Diseases 0.000 description 1
208000017442 Retinal disease Diseases 0.000 description 1
206010038923 Retinopathy Diseases 0.000 description 1
206010039710 Scleroderma Diseases 0.000 description 1
208000000453 Skin Neoplasms Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000005718 Stomach Neoplasms Diseases 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
208000023915 Ureteral Neoplasms Diseases 0.000 description 1
206010046431 Urethral cancer Diseases 0.000 description 1
206010046458 Urethral neoplasms Diseases 0.000 description 1
208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
201000005969 Uveal melanoma Diseases 0.000 description 1
201000003761 Vaginal carcinoma Diseases 0.000 description 1
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
201000005188 adrenal gland cancer Diseases 0.000 description 1
208000024447 adrenal gland neoplasm Diseases 0.000 description 1
229940009456 adriamycin Drugs 0.000 description 1
206010064930 age-related macular degeneration Diseases 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
230000001656 angiogenetic effect Effects 0.000 description 1
229940046836 anti-estrogen Drugs 0.000 description 1
230000001833 anti-estrogenic effect Effects 0.000 description 1
230000001028 anti-proliverative effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000001109 blastomere Anatomy 0.000 description 1
229960001561 bleomycin Drugs 0.000 description 1
OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000000133 brain stem Anatomy 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229960004562 carboplatin Drugs 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
208000019065 cervical carcinoma Diseases 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
208000012191 childhood neoplasm Diseases 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
208000037976 chronic inflammation Diseases 0.000 description 1
208000037893 chronic inflammatory disorder Diseases 0.000 description 1
208000024207 chronic leukemia Diseases 0.000 description 1
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
229960004316 cisplatin Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
208000030381 cutaneous melanoma Diseases 0.000 description 1
229960004397 cyclophosphamide Drugs 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000000750 endocrine system Anatomy 0.000 description 1
201000003914 endometrial carcinoma Diseases 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
201000001343 fallopian tube carcinoma Diseases 0.000 description 1
239000000945 filler Substances 0.000 description 1
229960002949 fluorouracil Drugs 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000006870 function Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
230000000762 glandular Effects 0.000 description 1
230000002518 glial effect Effects 0.000 description 1
208000005017 glioblastoma Diseases 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
201000010536 head and neck cancer Diseases 0.000 description 1
208000014829 head and neck neoplasm Diseases 0.000 description 1
201000011066 hemangioma Diseases 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
230000001096 hypoplastic effect Effects 0.000 description 1
230000002267 hypothalamic effect Effects 0.000 description 1
208000026278 immune system disease Diseases 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229940079322 interferon Drugs 0.000 description 1
201000002313 intestinal cancer Diseases 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
239000003446 ligand Substances 0.000 description 1
238000005567 liquid scintillation counting Methods 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
201000005202 lung cancer Diseases 0.000 description 1
208000020816 lung neoplasm Diseases 0.000 description 1
230000001926 lymphatic effect Effects 0.000 description 1
208000002780 macular degeneration Diseases 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000036210 malignancy Effects 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
208000026045 malignant tumor of parathyroid gland Diseases 0.000 description 1
239000000463 material Substances 0.000 description 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 description 1
210000000653 nervous system Anatomy 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
229940085033 nolvadex Drugs 0.000 description 1
201000002575 ocular melanoma Diseases 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
201000002528 pancreatic cancer Diseases 0.000 description 1
208000008443 pancreatic carcinoma Diseases 0.000 description 1
230000000849 parathyroid Effects 0.000 description 1
201000003913 parathyroid carcinoma Diseases 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
HTYIXCKSEQQCJO-UHFFFAOYSA-N phenaglycodol Chemical compound CC(C)(O)C(C)(O)C1=CC=C(Cl)C=C1 HTYIXCKSEQQCJO-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
208000016800 primary central nervous system lymphoma Diseases 0.000 description 1
230000008569 process Effects 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
201000008171 proliferative glomerulonephritis Diseases 0.000 description 1
230000009696 proliferative response Effects 0.000 description 1
201000004240 prostatic hypertrophy Diseases 0.000 description 1
229920005604 random copolymer Polymers 0.000 description 1
102000027426 receptor tyrosine kinases Human genes 0.000 description 1
108091008598 receptor tyrosine kinases Proteins 0.000 description 1
201000007444 renal pelvis carcinoma Diseases 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
230000011664 signaling Effects 0.000 description 1
230000007781 signaling event Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
201000000849 skin cancer Diseases 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
201000003708 skin melanoma Diseases 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000012089 stop solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229960001603 tamoxifen Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
208000013066 thyroid gland cancer Diseases 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
230000005747 tumor angiogenesis Effects 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
208000037965 uterine sarcoma Diseases 0.000 description 1
LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
210000003905 vulva Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen 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
- A61K31/495—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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis

NO20005453A 1998-04-29 2000-10-27 N-(3-etynylfenylamino)-6,7-bis(2-metoksyetoksy)-4-quinazolinamin mesylat anhydrat og monohydrat NO317301B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US8344198P	1998-04-29	1998-04-29
PCT/IB1999/000612 WO1999055683A1 (fr)	1998-04-29	1999-04-08	Anhydrate et monohydrate de n-(3-ethynylphenylamino)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine mesylate

Publications (3)

Publication Number	Publication Date
NO20005453D0 NO20005453D0 (no)	2000-10-27
NO20005453L NO20005453L (no)	2000-12-20
NO317301B1 true NO317301B1 (no)	2004-10-04

Family

ID=22178359

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20005453A NO317301B1 (no)	1998-04-29	2000-10-27	N-(3-etynylfenylamino)-6,7-bis(2-metoksyetoksy)-4-quinazolinamin mesylat anhydrat og monohydrat

Country Status (42)

Country	Link
EP (1)	EP1076652B1 (fr)
JP (1)	JP4652569B2 (fr)
KR (1)	KR100668412B1 (fr)
CN (2)	CN1298396A (fr)
AP (1)	AP1252A (fr)
AR (1)	AR018201A1 (fr)
AT (1)	ATE295839T1 (fr)
AU (1)	AU759691C (fr)
BR (1)	BR9910025A (fr)
CA (1)	CA2330447C (fr)
CO (1)	CO5060467A1 (fr)
CZ (1)	CZ298230B6 (fr)
DE (1)	DE69925366T2 (fr)
DZ (1)	DZ2777A1 (fr)
EA (1)	EA002836B1 (fr)
EG (1)	EG24000A (fr)
ES (1)	ES2238825T3 (fr)
GT (1)	GT199900063A (fr)
HK (1)	HK1037180A1 (fr)
HN (1)	HN1999000057A (fr)
HU (1)	HU227569B1 (fr)
ID (1)	ID27198A (fr)
IL (1)	IL139172A0 (fr)
MA (1)	MA26624A1 (fr)
ME (1)	MEP42008A (fr)
MX (1)	MXPA00010610A (fr)
MY (1)	MY136033A (fr)
NO (1)	NO317301B1 (fr)
NZ (1)	NZ508154A (fr)
OA (1)	OA11769A (fr)
PA (1)	PA8471001A1 (fr)
PE (1)	PE20000441A1 (fr)
PL (1)	PL196940B1 (fr)
RS (1)	RS50081B (fr)
SA (1)	SA99200216B1 (fr)
TN (1)	TNSN99079A1 (fr)
TR (1)	TR200003166T2 (fr)
TW (1)	TWI248437B (fr)
UA (1)	UA60363C2 (fr)
UY (1)	UY26099A1 (fr)
WO (1)	WO1999055683A1 (fr)
ZA (1)	ZA992972B (fr)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6706721B1 (en)	1998-04-29	2004-03-16	Osi Pharmaceuticals, Inc.	N-(3-ethynylphenylamino)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine mesylate anhydrate and monohydrate
YU13200A (sh)	1999-03-31	2002-10-18	Pfizer Products Inc.	Postupci i intermedijeri za dobijanje anti-kancernih jedinjenja
US7087613B2 (en)	1999-11-11	2006-08-08	Osi Pharmaceuticals, Inc.	Treating abnormal cell growth with a stable polymorph of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine hydrochloride
UA74803C2 (uk) *	1999-11-11	2006-02-15	Осі Фармасьютікалз, Інк.	Стійкий поліморф гідрохлориду n-(3-етинілфеніл)-6,7-біс(2-метоксіетокси)-4-хіназолінаміну, спосіб його одержання (варіанти) та фармацевтичне застосування
UA73993C2 (uk) *	2000-06-06	2005-10-17	Астразенека Аб	Хіназолінові похідні для лікування пухлин та фармацевтична композиція
AU2002350105A1 (en)	2001-06-21	2003-01-08	Ariad Pharmaceuticals, Inc.	Novel quinazolines and uses thereof
US7078409B2 (en)	2002-03-28	2006-07-18	Beta Pharma, Inc.	Fused quinazoline derivatives useful as tyrosine kinase inhibitors
GB0223854D0 (en) *	2002-10-12	2002-11-20	Astrazeneca Ab	Therapeutic treatment
US7148231B2 (en) *	2003-02-17	2006-12-12	Hoffmann-La Roche Inc.	[6,7-Bis(2-methoxy-ethoxy)-quinazolin-4-yl]-(3-ethynyl-phenyl)amine hydrochloride polymorph
MXPA05012939A (es)	2003-05-30	2006-05-17	Astrazeneca Uk Ltd	Procedimiento.
BRPI0411126A (pt)	2003-06-10	2006-07-18	Hoffmann La Roche	derivados de 1,3,4-triaza-fenaleno e 1,3,4,6-tetraazafenaleno
GB0403744D0 (en)	2004-02-20	2004-03-24	Astrazeneca Ab	Chemical process
CA2565721C (fr)	2004-05-06	2015-10-06	Bioresponse, L.L.C.	Preparations de diindolymethane destinee de traitement de leiomyomes
ATE497762T1 (de)	2004-12-30	2011-02-15	Bioresponse Llc	Verwendung von diindolylmethan-verwandten indolen zur behandlung und prävention von erkrankungen im zusammenhang mit dem respiratory syncytial virus
CA2659307A1 (fr)	2006-07-28	2008-01-31	Synthon B.V.	Forme cristalline d'erlobtinib
WO2008057253A2 (fr)	2006-10-27	2008-05-15	Bioresponse, L.L.C.	Procédés antiparasitaires et compositions utilisant des indoles associés au diindolylméthane
AU2008235274B2 (en) *	2007-04-04	2013-04-18	Cipla Limited	Process for preparation of erlotinib and its pharmaceutically acceptable salts
ES2492645T3 (es)	2007-07-11	2014-09-10	Hetero Drugs Limited	Un procedimiento mejorado para la preparación de hidrocloruro de erlotinib
WO2009024989A2 (fr)	2007-08-17	2009-02-26	Hetero Drugs Limited	Nouvelle forme hydratée de base libre d'erlotinib et procédé de préparation de la forme polymorphe a de chlorhydrate d'erlotinib sensiblement exempte de la forme polymorphe b
KR101132937B1 (ko) *	2008-10-01	2012-04-06	주식회사종근당	Ｎ-(3-에티닐페닐)-6,7-비스(2-메톡시에톡시)-4-퀴나졸린아민 납실레이트 염
US8440823B2 (en)	2009-03-26	2013-05-14	Ranbaxy Laboratories Limited	Process for the preparation of erlotinib or its pharmaceutically acceptable salts thereof
WO2011068404A2 (fr)	2009-12-02	2011-06-09	Ultimorphix Technologies B.V.	Administration par inhalation de sel de mésylate de n-(3-éthynylphénylamino)-6,7-bis(2-méthoxyéthoxy)-4-quinazolinamine
DE202010006543U1 (de)	2010-05-07	2010-09-09	Ratiopharm Gmbh	Erlotinibresinat
HU230483B1 (hu)	2011-10-10	2016-07-28	Egis Gyógyszergyár Nyrt.	Erlotinib sók
WO2014037961A1 (fr)	2012-09-04	2014-03-13	Shilpa Medicare Limited	Procédé de préparation de la forme cristalline de chlorhydrate d'erlotinib

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ243082A (en) *	1991-06-28	1995-02-24	Ici Plc	4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof
JP2994165B2 (ja) *	1992-06-26	1999-12-27	ゼネカ・リミテッド	キナゾリン誘導体、その製造法および該キナゾリン誘導体を含有する抗癌作用を得るための医薬調剤
GB9323290D0 (en) *	1992-12-10	1994-01-05	Zeneca Ltd	Quinazoline derivatives
ES2332984T3 (es) *	1995-03-30	2010-02-16	Pfizer Products Inc.	Derivados de quinazolinas.
US5747498A (en) *	1996-05-28	1998-05-05	Pfizer Inc.	Alkynyl and azido-substituted 4-anilinoquinazolines

1999
- 1999-04-08 JP JP2000545843A patent/JP4652569B2/ja not_active Expired - Lifetime
- 1999-04-08 RS YUP-661/00A patent/RS50081B/sr unknown
- 1999-04-08 CZ CZ20003974A patent/CZ298230B6/cs not_active IP Right Cessation
- 1999-04-08 MX MXPA00010610A patent/MXPA00010610A/es active IP Right Grant
- 1999-04-08 EP EP99909165A patent/EP1076652B1/fr not_active Expired - Lifetime
- 1999-04-08 AT AT99909165T patent/ATE295839T1/de not_active IP Right Cessation
- 1999-04-08 OA OA1200000300A patent/OA11769A/en unknown
- 1999-04-08 HU HU0101818A patent/HU227569B1/hu unknown
- 1999-04-08 BR BR9910025-8A patent/BR9910025A/pt not_active Application Discontinuation
- 1999-04-08 ES ES99909165T patent/ES2238825T3/es not_active Expired - Lifetime
- 1999-04-08 CN CN99805497A patent/CN1298396A/zh active Pending
- 1999-04-08 NZ NZ508154A patent/NZ508154A/en not_active IP Right Cessation
- 1999-04-08 AU AU28509/99A patent/AU759691C/en not_active Expired
- 1999-04-08 PL PL343766A patent/PL196940B1/pl not_active IP Right Cessation
- 1999-04-08 KR KR1020007011998A patent/KR100668412B1/ko not_active IP Right Cessation
- 1999-04-08 CA CA002330447A patent/CA2330447C/fr not_active Expired - Lifetime
- 1999-04-08 ID IDW20002186A patent/ID27198A/id unknown
- 1999-04-08 WO PCT/IB1999/000612 patent/WO1999055683A1/fr active IP Right Grant
- 1999-04-08 TR TR2000/03166T patent/TR200003166T2/xx unknown
- 1999-04-08 EA EA200001112A patent/EA002836B1/ru not_active IP Right Cessation
- 1999-04-08 DE DE69925366T patent/DE69925366T2/de not_active Expired - Lifetime
- 1999-04-08 CN CNA2008100051101A patent/CN101219999A/zh active Pending
- 1999-04-08 ME MEP-420/08A patent/MEP42008A/xx unknown
- 1999-04-08 IL IL13917299A patent/IL139172A0/xx not_active IP Right Cessation
- 1999-04-23 TW TW088106555A patent/TWI248437B/zh not_active IP Right Cessation
- 1999-04-26 HN HN1999000057A patent/HN1999000057A/es unknown
- 1999-04-27 PA PA19998471001A patent/PA8471001A1/es unknown
- 1999-04-27 AR ARP990101942A patent/AR018201A1/es active IP Right Grant
- 1999-04-27 MY MYPI99001636A patent/MY136033A/en unknown
- 1999-04-28 ZA ZA9902972A patent/ZA992972B/xx unknown
- 1999-04-28 DZ DZ990077A patent/DZ2777A1/fr active
- 1999-04-28 TN TNTNSN99079A patent/TNSN99079A1/fr unknown
- 1999-04-28 MA MA25557A patent/MA26624A1/fr unknown
- 1999-04-29 EG EG48299A patent/EG24000A/xx active
- 1999-04-29 CO CO99026003A patent/CO5060467A1/es unknown
- 1999-04-29 GT GT199900063A patent/GT199900063A/es unknown
- 1999-04-29 AP APAP/P/1999/001523A patent/AP1252A/en active
- 1999-04-29 PE PE1999000356A patent/PE20000441A1/es not_active Application Discontinuation
- 1999-06-02 SA SA99200216A patent/SA99200216B1/ar unknown
- 1999-08-04 UA UA2000116681A patent/UA60363C2/uk unknown
2000
- 2000-04-05 UY UY26099A patent/UY26099A1/es not_active Application Discontinuation
- 2000-10-27 NO NO20005453A patent/NO317301B1/no not_active IP Right Cessation
2001
- 2001-08-17 HK HK01105821A patent/HK1037180A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE69925366T2 (de)	2006-03-09
DZ2777A1 (fr)	2003-12-01
NZ508154A (en)	2003-07-25
UY26099A1 (es)	2001-12-28
YU66100A (sh)	2003-07-07
KR100668412B1 (ko)	2007-01-12
MA26624A1 (fr)	2004-12-20
NO20005453D0 (no)	2000-10-27
TNSN99079A1 (fr)	2005-11-10
ZA992972B (en)	2000-10-30
ATE295839T1 (de)	2005-06-15
MY136033A (en)	2008-07-31
IL139172A0 (en)	2001-11-25
SA99200216B1 (ar)	2006-06-04
PL343766A1 (en)	2001-09-10
ES2238825T3 (es)	2005-09-01
PL196940B1 (pl)	2008-02-29
AU759691B2 (en)	2003-04-17
KR20010078710A (ko)	2001-08-21
AP1252A (en)	2004-02-25
PA8471001A1 (es)	2000-09-29
EA200001112A1 (ru)	2001-04-23
JP4652569B2 (ja)	2011-03-16
WO1999055683A1 (fr)	1999-11-04
CO5060467A1 (es)	2001-07-30
AR018201A1 (es)	2001-10-31
AU759691C (en)	2004-04-29
PE20000441A1 (es)	2000-05-23
CZ20003974A3 (en)	2001-05-16
MEP42008A (en)	2011-02-10
GT199900063A (es)	2000-10-20
CN101219999A (zh)	2008-07-16
BR9910025A (pt)	2000-12-26
HUP0101818A3 (en)	2002-05-28
EP1076652B1 (fr)	2005-05-18
RS50081B (sr)	2009-01-22
UA60363C2 (uk)	2003-10-15
DE69925366D1 (de)	2005-06-23
TR200003166T2 (tr)	2001-02-21
AU2850999A (en)	1999-11-16
CZ298230B6 (cs)	2007-08-01
HU227569B1 (en)	2011-08-29
JP2002513009A (ja)	2002-05-08
HK1037180A1 (en)	2002-02-01
NO20005453L (no)	2000-12-20
MXPA00010610A (es)	2002-07-02
TWI248437B (en)	2006-02-01
HN1999000057A (es)	1999-09-29
EG24000A (en)	2008-03-19
HUP0101818A1 (hu)	2002-03-28
OA11769A (en)	2005-07-25
CN1298396A (zh)	2001-06-06
ID27198A (id)	2001-03-08
EA002836B1 (ru)	2002-10-31
AP9901523A0 (en)	1999-06-30
CA2330447C (fr)	2009-06-30
EP1076652A1 (fr)	2001-02-21
CA2330447A1 (fr)	1999-11-04

Legal Events

Date	Code	Title	Description
2013-12-02	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO317301B1 (no)	2004-10-04	N-(3-etynylfenylamino)-6,7-bis(2-metoksyetoksy)-4-quinazolinamin mesylat anhydrat og monohydrat
AU784243B2 (en)	2006-02-23	Stable polymorph of N-(3-ethynylphenyl)-6,7-bis (2-methoxyethoxy)-4-quinazolinamine hydrochloride, methods of production, and pharmaceutical uses thereof
WO1996033978A1 (fr)	1996-10-31	Derives de quinazoline
US6706721B1 (en)	2004-03-16	N-(3-ethynylphenylamino)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine mesylate anhydrate and monohydrate
ZA200203130B (en)	2003-04-22	Stable polymorph of N-(3-ethynylphenylamino)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine hydrochloride, methods of production, and pharmaceutical uses thereof.