UA75716C2 - Thiopene- and thiazolesulfonamides as antineoplastic agents, pharmaceutical composition based thereon - Google Patents

Thiopene- and thiazolesulfonamides as antineoplastic agents, pharmaceutical composition based thereon Download PDF

Info

Publication number: UA75716C2
Authority: UA; Ukraine
Prior art keywords: group; alkyl; halide; mixture; sulfamide
Prior art date: 2001-10-25

Application number

UA20040403046A

Other languages

English (en)

Ukrainian (uk)

Inventor

Cora Sue Grossman

Philip Arthur Hipskind

Karen Lynn Lobb

Jose Eduardo Lopez

Meri Margaret Mader

Michael Enrico Richett

Original Assignee

Lilly Co Eli

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.)

2001-10-25

Filing date

2002-10-15

Publication date

2006-05-15

2002-10-15 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

2006-05-15 Publication of UA75716C2 publication Critical patent/UA75716C2/uk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 8
239000002246 antineoplastic agent Substances 0.000 title description 3
229940034982 antineoplastic agent Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 113
206010028980 Neoplasm Diseases 0.000 claims description 77
229910052801 chlorine Inorganic materials 0.000 claims description 34
150000004820 halides Chemical class 0.000 claims description 27
239000000460 chlorine Substances 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
-1 CHNOCH" Chemical group 0.000 claims description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
210000001072 colon Anatomy 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
159000000000 sodium salts Chemical class 0.000 claims description 4
208000029742 colonic neoplasm Diseases 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
210000000664 rectum Anatomy 0.000 claims description 3
208000035269 cancer or benign tumor Diseases 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
229940126601 medicinal product Drugs 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
208000015634 Rectal Neoplasms Diseases 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
230000000118 anti-neoplastic effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 102
239000000203 mixture Substances 0.000 description 94
239000000243 solution Substances 0.000 description 83
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 72
230000015572 biosynthetic process Effects 0.000 description 56
238000003786 synthesis reaction Methods 0.000 description 56
239000011541 reaction mixture Substances 0.000 description 52
235000019439 ethyl acetate Nutrition 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
238000005481 NMR spectroscopy Methods 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
125000001309 chloro group Chemical group Cl* 0.000 description 27
239000012267 brine Substances 0.000 description 26
239000012044 organic layer Substances 0.000 description 26
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
238000000034 method Methods 0.000 description 24
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
239000000284 extract Substances 0.000 description 20
239000000741 silica gel Substances 0.000 description 19
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
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239000010410 layer Substances 0.000 description 18
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239000012043 crude product Substances 0.000 description 15
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230000002829 reductive effect Effects 0.000 description 15
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RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 11
239000003480 eluent Substances 0.000 description 11
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229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
239000007787 solid Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
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241000124008 Mammalia Species 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
239000000725 suspension Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
239000000126 substance Substances 0.000 description 8
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 8
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238000001914 filtration Methods 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-Chlorosuccinimide Substances ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
229910002091 carbon monoxide Inorganic materials 0.000 description 6
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
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241001465754 Metazoa Species 0.000 description 5
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125000001246 bromo group Chemical group Br* 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
238000004949 mass spectrometry Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
238000010791 quenching Methods 0.000 description 5
108091003079 Bovine Serum Albumin Proteins 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
230000033115 angiogenesis Effects 0.000 description 4
230000037396 body weight Effects 0.000 description 4
201000011510 cancer Diseases 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
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NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
239000003826 tablet Substances 0.000 description 4
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FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
VPXDRKKLIQLLJO-UHFFFAOYSA-N 3-hydroxy-5-(trifluoromethyl)thiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C(F)(F)F)=CC=1O VPXDRKKLIQLLJO-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical compound OCC1=CC=CS1 ZPHGMBGIFODUMF-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/36—Sulfur atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

UA20040403046A 2001-10-25 2002-10-15 Thiopene- and thiazolesulfonamides as antineoplastic agents, pharmaceutical composition based thereon UA75716C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US35201201P	2001-10-25	2001-10-25
PCT/US2002/031568 WO2003035629A1 (fr)	2001-10-25	2002-10-15	Antineoplasiques a base de thiopenesulfonamides et de thiazolesulfonamides

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Publication Number	Publication Date
UA75716C2 true UA75716C2 (en)	2006-05-15

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US (2)	US7084170B2 (fr)
EP (1)	EP1442030B1 (fr)
JP (1)	JP4464681B2 (fr)
KR (1)	KR100913471B1 (fr)
CN (1)	CN1298709C (fr)
AR (1)	AR037248A1 (fr)
AT (1)	ATE338033T1 (fr)
AU (1)	AU2002334817B2 (fr)
BR (1)	BR0212386A (fr)
CA (1)	CA2463300C (fr)
CY (1)	CY1106247T1 (fr)
DE (1)	DE60214413T2 (fr)
DK (1)	DK1442030T3 (fr)
EA (1)	EA006081B1 (fr)
EC (1)	ECSP045078A (fr)
EG (1)	EG26021A (fr)
ES (1)	ES2269816T3 (fr)
HR (1)	HRP20040371B1 (fr)
HU (1)	HUP0401638A3 (fr)
IL (2)	IL160851A0 (fr)
MX (1)	MXPA04003886A (fr)
MY (1)	MY130718A (fr)
NO (1)	NO20041316L (fr)
NZ (1)	NZ531136A (fr)
PE (1)	PE20030574A1 (fr)
PL (1)	PL208083B1 (fr)
PT (1)	PT1442030E (fr)
SI (1)	SI1442030T1 (fr)
SV (1)	SV2004001367A (fr)
TW (1)	TWI281916B (fr)
UA (1)	UA75716C2 (fr)
WO (1)	WO2003035629A1 (fr)
ZA (1)	ZA200403089B (fr)

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AP1753A (en) *	2001-06-11	2007-07-18	Shire Biochem Inc	Thiophene derivatives as antiviral agents for flavvivirus infection
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Publication number	Publication date
US20040198784A1 (en)	2004-10-07
JP2005511547A (ja)	2005-04-28
HK1068337A1 (en)	2005-04-29
IL160851A (en)	2009-11-18
AR037248A1 (es)	2004-11-03
ECSP045078A (es)	2004-06-28
CN1575286A (zh)	2005-02-02
HRP20040371A2 (en)	2004-08-31
PE20030574A1 (es)	2003-07-03
CA2463300C (fr)	2011-07-19
TWI281916B (en)	2007-06-01
AU2002334817B2 (en)	2008-02-21
PT1442030E (pt)	2006-12-29
KR100913471B1 (ko)	2009-08-25
CY1106247T1 (el)	2011-06-08
HRP20040371B1 (en)	2012-07-31
HUP0401638A3 (en)	2012-09-28
EP1442030B1 (fr)	2006-08-30
IL160851A0 (en)	2004-08-31
PL208083B1 (pl)	2011-03-31
SI1442030T1 (sl)	2006-12-31
DE60214413T2 (de)	2007-03-08
EG26021A (en)	2012-12-10
MY130718A (en)	2007-07-31
NZ531136A (en)	2006-08-31
DE60214413D1 (de)	2006-10-12
HUP0401638A2 (hu)	2004-11-29
US7250430B2 (en)	2007-07-31
BR0212386A (pt)	2004-07-27
ES2269816T3 (es)	2007-04-01
PL368234A1 (en)	2005-03-21
ZA200403089B (en)	2005-04-22
EA200400582A1 (ru)	2004-08-26
KR20040062583A (ko)	2004-07-07
EA006081B1 (ru)	2005-08-25
ATE338033T1 (de)	2006-09-15
WO2003035629A1 (fr)	2003-05-01
EP1442030A1 (fr)	2004-08-04
MXPA04003886A (es)	2004-07-08
CA2463300A1 (fr)	2003-05-01
CN1298709C (zh)	2007-02-07
NO20041316L (no)	2004-03-30
US7084170B2 (en)	2006-08-01
US20060223871A1 (en)	2006-10-05
DK1442030T3 (da)	2006-12-27
SV2004001367A (es)	2004-02-24
JP4464681B2 (ja)	2010-05-19

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