SK286405B6 - Derivát izotiazolu, spôsob a medziprodukty na jeho prípravu a farmaceutická kompozícia s jeho obsahom na liečenie hyperproliferatívnych chorôb - Google Patents

Derivát izotiazolu, spôsob a medziprodukty na jeho prípravu a farmaceutická kompozícia s jeho obsahom na liečenie hyperproliferatívnych chorôb Download PDF

Info

Publication number: SK286405B6
Authority: SK; Slovakia
Prior art keywords: isothiazole; ureido; benzyloxy; carboxamide; methyl
Prior art date: 1998-06-04

Application number

SK1778-2000A

Other languages

English (en)

Slovak (sk)

Other versions

SK17782000A3 (sk

Inventor

Eric Robert Larson

Mark Carl Noe

Thomas George Gant

Original Assignee

Pfizer Products 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.)

1998-06-04

Filing date

1999-05-03

Publication date

2008-09-05

1999-05-03 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2001-08-06 Publication of SK17782000A3 publication Critical patent/SK17782000A3/sk

2008-09-05 Publication of SK286405B6 publication Critical patent/SK286405B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 34
150000003854 isothiazoles Chemical class 0.000 title claims abstract description 32
238000002360 preparation method Methods 0.000 title claims abstract description 22
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 18
230000003463 hyperproliferative effect Effects 0.000 title claims abstract description 16
239000003814 drug Substances 0.000 claims abstract description 12
238000004519 manufacturing process Methods 0.000 claims abstract description 8
-1 morpholino, pyrrolidinyl Chemical group 0.000 claims description 522
150000001875 compounds Chemical class 0.000 claims description 204
125000000623 heterocyclic group Chemical group 0.000 claims description 72
125000003118 aryl group Chemical group 0.000 claims description 59
150000003839 salts Chemical class 0.000 claims description 48
125000000217 alkyl group Chemical group 0.000 claims description 35
125000004434 sulfur atom Chemical group 0.000 claims description 34
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 28
229910052717 sulfur Inorganic materials 0.000 claims description 24
125000004430 oxygen atom Chemical group O* 0.000 claims description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
201000010099 disease Diseases 0.000 claims description 20
229910052760 oxygen Inorganic materials 0.000 claims description 20
125000004122 cyclic group Chemical group 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
125000005842 heteroatom Chemical group 0.000 claims description 18
125000001424 substituent group Chemical group 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
BEPMYBTTZSNHPS-UHFFFAOYSA-N 1,2-thiazole-4-carboxamide Chemical compound NC(=O)C=1C=NSC=1 BEPMYBTTZSNHPS-UHFFFAOYSA-N 0.000 claims description 12
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 10
201000011510 cancer Diseases 0.000 claims description 9
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
210000002307 prostate Anatomy 0.000 claims description 9
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 8
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
239000012453 solvate Substances 0.000 claims description 8
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
QMLVECGLEOSESV-RYUDHWBXSA-N Danofloxacin Chemical compound C([C@@H]1C[C@H]2CN1C)N2C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=CC=1N2C1CC1 QMLVECGLEOSESV-RYUDHWBXSA-N 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
239000003112 inhibitor Substances 0.000 claims description 7
210000004072 lung Anatomy 0.000 claims description 7
OPKHOMGGMCLBCP-UHFFFAOYSA-N 5-[3-(4-methylpiperazin-1-yl)propylcarbamoylamino]-3-[(2,3,6-trifluoro-4-methylphenyl)methoxy]-1,2-thiazole-4-carboxamide Chemical compound C1CN(C)CCN1CCCNC(=O)NC1=C(C(N)=O)C(OCC=2C(=C(F)C(C)=CC=2F)F)=NS1 OPKHOMGGMCLBCP-UHFFFAOYSA-N 0.000 claims description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
210000000481 breast Anatomy 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
210000000496 pancreas Anatomy 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
102000004190 Enzymes Human genes 0.000 claims description 5
108090000790 Enzymes Proteins 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
206010041823 squamous cell carcinoma Diseases 0.000 claims description 5
208000009849 Female Genital Neoplasms Diseases 0.000 claims description 4
208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
230000000340 anti-metabolite Effects 0.000 claims description 4
239000002256 antimetabolite Substances 0.000 claims description 4
229940100197 antimetabolite Drugs 0.000 claims description 4
239000002246 antineoplastic agent Substances 0.000 claims description 4
210000004556 brain Anatomy 0.000 claims description 4
239000003102 growth factor Substances 0.000 claims description 4
210000003128 head Anatomy 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
230000011278 mitosis Effects 0.000 claims description 4
210000003739 neck Anatomy 0.000 claims description 4
230000002611 ovarian Effects 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
210000002784 stomach Anatomy 0.000 claims description 4
210000003932 urinary bladder Anatomy 0.000 claims description 4
HXHAJRMTJXHJJZ-UHFFFAOYSA-N 3-[(4-bromo-2,6-difluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=CC(Br)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CCCC1 HXHAJRMTJXHJJZ-UHFFFAOYSA-N 0.000 claims description 3
MUMZOQWBQONBKS-UHFFFAOYSA-N 5-(methylcarbamoylamino)-3-propylsulfanyl-1,2-thiazole-4-carboxamide Chemical compound CCCSC1=NSC(NC(=O)NC)=C1C(N)=O MUMZOQWBQONBKS-UHFFFAOYSA-N 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
229940123587 Cell cycle inhibitor Drugs 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
230000002280 anti-androgenic 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
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
206010020718 hyperplasia Diseases 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000004193 piperazinyl group Chemical group 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
208000013076 thyroid tumor Diseases 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
VGFOJFVFHLTSSU-UHFFFAOYSA-N 5-(dimethylcarbamoylamino)-3-ethylsulfanyl-1,2-thiazole-4-carboxamide Chemical compound CCSC1=NSC(NC(=O)N(C)C)=C1C(N)=O VGFOJFVFHLTSSU-UHFFFAOYSA-N 0.000 claims description 2
KTXCVYMMHAFUTM-UHFFFAOYSA-N 5-(dimethylcarbamoylamino)-3-propylsulfanyl-1,2-thiazole-4-carboxamide Chemical compound CCCSC1=NSC(NC(=O)N(C)C)=C1C(N)=O KTXCVYMMHAFUTM-UHFFFAOYSA-N 0.000 claims description 2
WJMRRSQFRXEXHM-UHFFFAOYSA-N 5-(methylcarbamoylamino)-3-methylsulfanyl-1,2-thiazole-4-carboxamide Chemical compound CNC(=O)NC=1SN=C(SC)C=1C(N)=O WJMRRSQFRXEXHM-UHFFFAOYSA-N 0.000 claims description 2
LVWQIZCZUXJWTN-UHFFFAOYSA-N Cl.S1N=CC(=C1)C(=O)N Chemical compound Cl.S1N=CC(=C1)C(=O)N LVWQIZCZUXJWTN-UHFFFAOYSA-N 0.000 claims description 2
208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 2
108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 2
150000003857 carboxamides Chemical class 0.000 claims description 2
229940111134 coxibs Drugs 0.000 claims description 2
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 2
239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 2
229940121647 egfr inhibitor Drugs 0.000 claims description 2
229940088598 enzyme Drugs 0.000 claims description 2
239000000367 immunologic factor Substances 0.000 claims description 2
239000012444 intercalating antibiotic Substances 0.000 claims description 2
210000003734 kidney Anatomy 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000003367 polycyclic group Chemical group 0.000 claims description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
239000002464 receptor antagonist Substances 0.000 claims description 2
229940044551 receptor antagonist Drugs 0.000 claims description 2
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 claims description 2
229940044693 topoisomerase inhibitor Drugs 0.000 claims description 2
208000001333 Colorectal Neoplasms Diseases 0.000 claims 2
BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 claims 2
208000025402 neoplasm of esophagus Diseases 0.000 claims 2
FLIJOUHDTCIKLC-UHFFFAOYSA-N 3-ethoxy-5-(methylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound CCOC1=NSC(NC(=O)NC)=C1C(N)=O FLIJOUHDTCIKLC-UHFFFAOYSA-N 0.000 claims 1
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 claims 1
XTOWBIWKPBDEQA-UHFFFAOYSA-N 5-(carbamoylamino)-3-ethylsulfanyl-1,2-thiazole-4-carboxamide Chemical compound C(N)(=O)C=1C(=NSC=1NC(N)=O)SCC XTOWBIWKPBDEQA-UHFFFAOYSA-N 0.000 claims 1
QPMSKYRIMDNSHI-UHFFFAOYSA-N 5-(carbamoylamino)-3-propan-2-ylsulfanyl-1,2-thiazole-4-carboxamide Chemical compound C(N)(=O)C=1C(=NSC=1NC(N)=O)SC(C)C QPMSKYRIMDNSHI-UHFFFAOYSA-N 0.000 claims 1
208000035475 disorder Diseases 0.000 claims 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 description 97
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238000005481 NMR spectroscopy Methods 0.000 description 70
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SYGTUWWBOUMVHV-UHFFFAOYSA-N phenyl n-[4-carbamoyl-3-[(2,5-difluoro-4-methylphenyl)methoxy]-1,2-thiazol-5-yl]carbamate Chemical compound C1=C(F)C(C)=CC(F)=C1COC1=NSC(NC(=O)OC=2C=CC=CC=2)=C1C(N)=O SYGTUWWBOUMVHV-UHFFFAOYSA-N 0.000 description 18
239000002253 acid Substances 0.000 description 15
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LUGNUVHQIIOEJH-UHFFFAOYSA-N phenyl n-[4-carbamoyl-3-[(2,3,6-trifluoro-4-methylphenyl)methoxy]-1,2-thiazol-5-yl]carbamate Chemical compound FC1=C(F)C(C)=CC(F)=C1COC1=NSC(NC(=O)OC=2C=CC=CC=2)=C1C(N)=O LUGNUVHQIIOEJH-UHFFFAOYSA-N 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000010410 layer Substances 0.000 description 12
HEQLLJSEFFOOCM-UHFFFAOYSA-N phenyl n-[4-carbamoyl-3-[(2,6-difluoro-4-methylphenyl)methoxy]-1,2-thiazol-5-yl]carbamate Chemical compound FC1=CC(C)=CC(F)=C1COC1=NSC(NC(=O)OC=2C=CC=CC=2)=C1C(N)=O HEQLLJSEFFOOCM-UHFFFAOYSA-N 0.000 description 12
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
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239000011593 sulfur Substances 0.000 description 5
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125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 1
PEPCYJSDHYMIFN-UHFFFAOYSA-N 4-chloro-2,5-difluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(Cl)C=C1F PEPCYJSDHYMIFN-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
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125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
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YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
238000012216 screening Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
201000000849 skin cancer Diseases 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940048086 sodium pyrophosphate Drugs 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
229960001603 tamoxifen Drugs 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
UDEJEOLNSNYQSX-UHFFFAOYSA-J tetrasodium;2,4,6,8-tetraoxido-1,3,5,7,2$l^{5},4$l^{5},6$l^{5},8$l^{5}-tetraoxatetraphosphocane 2,4,6,8-tetraoxide Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P1(=O)OP([O-])(=O)OP([O-])(=O)OP([O-])(=O)O1 UDEJEOLNSNYQSX-UHFFFAOYSA-J 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003567 thiocyanates Chemical class 0.000 description 1
201000002510 thyroid cancer Diseases 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000026683 transduction Effects 0.000 description 1
238000010361 transduction Methods 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 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
229910052722 tritium Inorganic materials 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
230000004565 tumor cell growth Effects 0.000 description 1
210000003606 umbilical vein Anatomy 0.000 description 1
241000701447 unidentified baculovirus Species 0.000 description 1
210000000626 ureter Anatomy 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
208000037965 uterine sarcoma Diseases 0.000 description 1
210000004291 uterus Anatomy 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
208000013013 vulvar carcinoma Diseases 0.000 description 1
239000011534 wash buffer Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- 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
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/58—Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07D487/08—Bridged systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Urology & Nephrology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK1778-2000A 1998-06-04 1999-05-03 Derivát izotiazolu, spôsob a medziprodukty na jeho prípravu a farmaceutická kompozícia s jeho obsahom na liečenie hyperproliferatívnych chorôb SK286405B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US8796398P	1998-06-04	1998-06-04
PCT/IB1999/000797 WO1999062890A1 (fr)	1998-06-04	1999-05-03	Derives isothiazole utiles en tant qu'agents anticancereux

Publications (2)

Publication Number	Publication Date
SK17782000A3 SK17782000A3 (sk)	2001-08-06
SK286405B6 true SK286405B6 (sk)	2008-09-05

Family

ID=22208298

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1778-2000A SK286405B6 (sk)	1998-06-04	1999-05-03	Derivát izotiazolu, spôsob a medziprodukty na jeho prípravu a farmaceutická kompozícia s jeho obsahom na liečenie hyperproliferatívnych chorôb

Country Status (45)

Country	Link
US (4)	US6235764B1 (fr)
EP (1)	EP1084114B1 (fr)
JP (2)	JP3735254B2 (fr)
KR (1)	KR100392434B1 (fr)
CN (2)	CN1172918C (fr)
AP (1)	AP1309A (fr)
AR (1)	AR016725A1 (fr)
AT (1)	ATE275553T1 (fr)
AU (1)	AU3342199A (fr)
BG (1)	BG65104B1 (fr)
BR (1)	BR9910900B1 (fr)
CA (2)	CA2475113C (fr)
CO (1)	CO5011121A1 (fr)
CZ (1)	CZ298559B6 (fr)
DE (1)	DE69920009T2 (fr)
EA (1)	EA004935B1 (fr)
ES (1)	ES2226368T3 (fr)
GE (1)	GEP20084337B (fr)
GT (1)	GT199900070A (fr)
HN (1)	HN1999000080A (fr)
HR (1)	HRP20000835B1 (fr)
HU (1)	HUP0102422A3 (fr)
ID (1)	ID27006A (fr)
IL (1)	IL138776A0 (fr)
IS (1)	IS2269B (fr)
MA (1)	MA26638A1 (fr)
MY (1)	MY130668A (fr)
NO (1)	NO318798B1 (fr)
NZ (1)	NZ507009A (fr)
OA (1)	OA11504A (fr)
PA (1)	PA8472301A1 (fr)
PE (1)	PE20000568A1 (fr)
PL (1)	PL198151B1 (fr)
PT (1)	PT1084114E (fr)
SA (1)	SA99200217B1 (fr)
SI (1)	SI1084114T1 (fr)
SK (1)	SK286405B6 (fr)
TN (1)	TNSN99106A1 (fr)
TR (1)	TR200003478T2 (fr)
TW (1)	TW561154B (fr)
UA (1)	UA60365C2 (fr)
UY (1)	UY25619A1 (fr)
WO (1)	WO1999062890A1 (fr)
YU (1)	YU70100A (fr)
ZA (1)	ZA993752B (fr)

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1999
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Publication number	Publication date
HN1999000080A (es)	1999-09-29
DE69920009T2 (de)	2005-09-15
CA2475113A1 (fr)	1999-12-09
JP2005002122A (ja)	2005-01-06
SK17782000A3 (sk)	2001-08-06
HK1036982A1 (en)	2002-01-25
AP9901560A0 (en)	1999-06-30
TR200003478T2 (tr)	2001-03-21
WO1999062890A1 (fr)	1999-12-09
PT1084114E (pt)	2004-12-31
SI1084114T1 (en)	2005-02-28
US7405218B2 (en)	2008-07-29
EP1084114A1 (fr)	2001-03-21
JP2002517384A (ja)	2002-06-18
US20010020034A1 (en)	2001-09-06
PA8472301A1 (es)	2000-09-29
CA2475113C (fr)	2008-03-18
JP3735254B2 (ja)	2006-01-18
MY130668A (en)	2007-07-31
BR9910900A (pt)	2001-02-13
AU3342199A (en)	1999-12-20
US7790902B2 (en)	2010-09-07
US20030149048A1 (en)	2003-08-07
HUP0102422A2 (hu)	2002-05-29
GEP20084337B (fr)	2008-03-25
HUP0102422A3 (en)	2002-06-28
US20080300249A1 (en)	2008-12-04
PL198151B1 (pl)	2008-05-30
BG65104B1 (bg)	2007-02-28
NO20006071D0 (no)	2000-11-30
CA2333703C (fr)	2005-06-14
KR100392434B1 (ko)	2003-07-22
MA26638A1 (fr)	2004-12-20
CN1172918C (zh)	2004-10-27
YU70100A (sh)	2004-07-15
AR016725A1 (es)	2001-07-25
EA200001146A1 (ru)	2001-04-23
NO20006071L (no)	2000-11-30
ATE275553T1 (de)	2004-09-15
HRP20000835B1 (hr)	2008-01-31
CA2333703A1 (fr)	1999-12-09
ZA993752B (en)	2000-12-04
PL344691A1 (en)	2001-11-19
UY25619A1 (es)	2000-02-23
US6235764B1 (en)	2001-05-22
KR20010052516A (ko)	2001-06-25
OA11504A (en)	2004-05-17
CO5011121A1 (es)	2001-02-28
US6548526B2 (en)	2003-04-15
HRP20000835A2 (en)	2001-12-31
IL138776A0 (en)	2001-10-31
EA004935B1 (ru)	2004-10-28
SA99200217B1 (ar)	2006-05-06
NO318798B1 (no)	2005-05-09
NZ507009A (en)	2003-11-28
UA60365C2 (uk)	2003-10-15
CN1303380A (zh)	2001-07-11
DE69920009D1 (de)	2004-10-14
BR9910900B1 (pt)	2013-09-17
AP1309A (en)	2004-09-14
TNSN99106A1 (fr)	2005-11-10
IS5690A (is)	2000-10-27
ID27006A (id)	2001-02-22
CZ298559B6 (cs)	2007-11-07
CZ20004451A3 (en)	2001-05-16
GT199900070A (es)	2000-11-10
EP1084114B1 (fr)	2004-09-08
IS2269B (is)	2007-07-15
PE20000568A1 (es)	2000-07-08
ES2226368T3 (es)	2005-03-16
TW561154B (en)	2003-11-11
BG104998A (en)	2001-07-31
CN1616386A (zh)	2005-05-18

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SK286405B6 (sk)	2008-09-05	Derivát izotiazolu, spôsob a medziprodukty na jeho prípravu a farmaceutická kompozícia s jeho obsahom na liečenie hyperproliferatívnych chorôb
JP3692041B2 (ja)	2005-09-07	抗がん剤として有用な複素環式誘導体
DE60113283T2 (de)	2006-06-08	Thiadiazole und oxadiazole sowie ihre verwendung als phosphodiesterase-7 inhibitoren
JP2023518774A (ja)	2023-05-08	置換ピリミジンまたはピリジルアミン誘導体、その組成物及び医薬的使用
DE69717453T2 (de)	2003-07-10	Amid derivate
CN101043888B (zh)	2010-08-11	制备异噻唑衍生物的方法
EP2070927A1 (fr)	2009-06-17	Dérivé hétérocyclique fusionné
WO2019149205A1 (fr)	2019-08-08	Dérivé de benzohétéroaryle et son procédé de préparation et son application médicale
Dong et al.	2002	The syntheses and crystal structure of novel 5-methyl-3-substituted-1, 2, 4-triazolo [3, 4-b] benzothiazoles
MXPA00011849A (en)	2001-09-07	Isothiazole derivatives useful as anticancer agents
AU2004202433B2 (en)	2007-04-19	Isothiazole Derivatives Useful as Anticancer Agents
EP0502885B1 (fr)	1994-06-01	Composes d'imidazoquinoxaline, leur preparation et emploi
AU2007203344A1 (en)	2007-08-09	Isothiazole derivatives useful as anticancer agents
NZ754385A (en)	2024-07-05	Poly-adp ribose polymerase (parp) inhibitors

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