CA2838029A1 - Heterocyclic sulfonamide derivatives - Google Patents

Heterocyclic sulfonamide derivatives Download PDF

Info

Publication number: CA2838029A1
Authority: CA; Canada
Prior art keywords: compound; compounds; fluoro; difluoro; iodophenyl
Prior art date: 2011-06-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA2838029A

Other languages

English (en)

French (fr)

Inventor

Ramulu Poddutoori

Can Wang

Xianglin ZHAO

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Novartis AG

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.)

2011-06-09

Filing date

2012-06-06

Publication date

2012-12-13

2012-06-06 Application filed by Novartis AG filed Critical Novartis AG

2012-12-13 Publication of CA2838029A1 publication Critical patent/CA2838029A1/en

Status Abandoned legal-status Critical Current

Links

-1 Heterocyclic sulfonamide Chemical class 0.000 title claims description 34
229940124530 sulfonamide Drugs 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims abstract description 199
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
206010028980 Neoplasm Diseases 0.000 claims abstract description 26
238000011282 treatment Methods 0.000 claims abstract description 26
239000003112 inhibitor Substances 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 15
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238000000034 method Methods 0.000 claims description 28
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108091054455 MAP kinase family Proteins 0.000 claims description 26
239000003814 drug Substances 0.000 claims description 25
239000008194 pharmaceutical composition Substances 0.000 claims description 15
229940124597 therapeutic agent Drugs 0.000 claims description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 claims description 12
208000035475 disorder Diseases 0.000 claims description 12
239000000546 pharmaceutical excipient Substances 0.000 claims description 11
XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 claims description 10
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 8
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ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 6
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FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
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KVJXBPDAXMEYOA-CXANFOAXSA-N trilostane Chemical compound OC1=C(C#N)C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@@]32O[C@@H]31 KVJXBPDAXMEYOA-CXANFOAXSA-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
208000022271 tubular adenoma Diseases 0.000 description 1
238000007492 two-way ANOVA Methods 0.000 description 1
TUCIOBMMDDOEMM-RIYZIHGNSA-N tyrphostin B42 Chemical compound C1=C(O)C(O)=CC=C1\C=C(/C#N)C(=O)NCC1=CC=CC=C1 TUCIOBMMDDOEMM-RIYZIHGNSA-N 0.000 description 1
230000036967 uncompetitive effect Effects 0.000 description 1
208000009852 uremia Diseases 0.000 description 1
201000005645 urethra squamous cell carcinoma Diseases 0.000 description 1
VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(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]([C@@H](C)O)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](CCCNC(N)=N)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)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)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=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
229960002004 valdecoxib Drugs 0.000 description 1
LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
229960000241 vandetanib Drugs 0.000 description 1
YCOYDOIWSSHVCK-UHFFFAOYSA-N vatalanib Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1CC1=CC=NC=C1 YCOYDOIWSSHVCK-UHFFFAOYSA-N 0.000 description 1
229940099039 velcade Drugs 0.000 description 1
YTZALCGQUPRCGW-ZSFNYQMMSA-N verteporfin Chemical compound N1C(C=C2C(=C(CCC(O)=O)C(C=C3C(CCC(=O)OC)=C(C)C(N3)=C3)=N2)C)=C(C=C)C(C)=C1C=C1C2=CC=C(C(=O)OC)[C@@H](C(=O)OC)[C@@]2(C)C3=N1 YTZALCGQUPRCGW-ZSFNYQMMSA-N 0.000 description 1
230000035899 viability Effects 0.000 description 1
208000009540 villous adenoma Diseases 0.000 description 1
JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine 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-CFWMRBGOSA-N 0.000 description 1
NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
229960000922 vinflunine Drugs 0.000 description 1
229940061392 visudyne Drugs 0.000 description 1
208000030401 vitamin deficiency disease Diseases 0.000 description 1
229960001771 vorozole Drugs 0.000 description 1
XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229940053867 xeloda Drugs 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
229940033942 zoladex Drugs 0.000 description 1
229940002005 zometa Drugs 0.000 description 1
229950009819 zotarolimus Drugs 0.000 description 1
CGTADGCBEXYWNE-JUKNQOCSSA-N zotarolimus Chemical compound N1([C@H]2CC[C@@H](C[C@@H](C)[C@H]3OC(=O)[C@@H]4CCCCN4C(=O)C(=O)[C@@]4(O)[C@H](C)CC[C@H](O4)C[C@@H](/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C3)OC)C[C@H]2OC)C=NN=N1 CGTADGCBEXYWNE-JUKNQOCSSA-N 0.000 description 1
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Psychiatry (AREA)
Rheumatology (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Furan Compounds (AREA)

CA2838029A 2011-06-09 2012-06-06 Heterocyclic sulfonamide derivatives Abandoned CA2838029A1 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
IN1634/DEL/11		2011-06-09
IN1634DE2011		2011-06-09
CN201210175145.6		2012-05-31
CN201210175145		2012-05-31
PCT/IB2012/052860 WO2012168884A1 (en)	2011-06-09	2012-06-06	Heterocyclic sulfonamide derivatives

Publications (1)

Publication Number	Publication Date
CA2838029A1 true CA2838029A1 (en)	2012-12-13

Family

ID=46384435

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2838029A Abandoned CA2838029A1 (en)	2011-06-09	2012-06-06	Heterocyclic sulfonamide derivatives

Country Status (10)

Country	Link
EP (1)	EP2718276A1 (2)
JP (1)	JP2014517004A (2)
KR (1)	KR20140034898A (2)
AU (1)	AU2012265844A1 (2)
BR (1)	BR112013031201A2 (2)
CA (1)	CA2838029A1 (2)
EA (1)	EA201391820A1 (2)
IN (1)	IN2014DN00123A (2)
MX (1)	MX2013014398A (2)
WO (1)	WO2012168884A1 (2)

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CN104886052B (zh) *	2015-06-02	2016-08-31	吉林省八达农药有限公司	一种环丙磺酰胺的应用
CN110869357A (zh) *	2017-05-25	2020-03-06	亚瑞克西斯制药公司	化合物及其用于治疗癌症的使用方法
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2012
- 2012-06-06 EA EA201391820A patent/EA201391820A1/ru unknown
- 2012-06-06 WO PCT/IB2012/052860 patent/WO2012168884A1/en not_active Ceased
- 2012-06-06 MX MX2013014398A patent/MX2013014398A/es unknown
- 2012-06-06 BR BR112013031201A patent/BR112013031201A2/pt not_active IP Right Cessation
- 2012-06-06 IN IN123DEN2014 patent/IN2014DN00123A/en unknown
- 2012-06-06 CA CA2838029A patent/CA2838029A1/en not_active Abandoned
- 2012-06-06 JP JP2014514204A patent/JP2014517004A/ja active Pending
- 2012-06-06 KR KR1020147000283A patent/KR20140034898A/ko not_active Withdrawn
- 2012-06-06 EP EP12730043.2A patent/EP2718276A1/en not_active Withdrawn
- 2012-06-06 AU AU2012265844A patent/AU2012265844A1/en not_active Abandoned

Also Published As

Publication number	Publication date
EA201391820A1 (ru)	2014-12-30
JP2014517004A (ja)	2014-07-17
EP2718276A1 (en)	2014-04-16
IN2014DN00123A (2)	2015-05-22
WO2012168884A1 (en)	2012-12-13
AU2012265844A1 (en)	2013-05-02
MX2013014398A (es)	2014-03-21
KR20140034898A (ko)	2014-03-20
BR112013031201A2 (pt)	2017-01-31

Legal Events

Date	Code	Title	Description
2016-07-20	FZDE	Discontinued	Effective date: 20160608

Publication	Publication Date	Title
US8466289B2 (en)	2013-06-18	Heterocyclic sulfonamide derivatives
KR20120028882A (ko)	2012-03-23	Ｍｅｋ 억제제로서의 헤테로시클릭 화합물
WO2012066095A1 (en)	2012-05-24	Crystalline form of an inhibitor of mdm2/4 and p53 interaction
US20090275606A1 (en)	2009-11-05	Heterocyclic Compounds as MEK Inhibitors
AU2010329940B2 (en)	2013-05-16	Heterocyclic sulfonamide derivatives
CA2838029A1 (en)	2012-12-13	Heterocyclic sulfonamide derivatives
WO2015022664A1 (en)	2015-02-19	Compounds and compositions as inhibitors of mek
US8470878B2 (en)	2013-06-25	Heterocyclic sulfonamide derivatives
WO2015022663A1 (en)	2015-02-19	Compounds and compositions as inhibitors of mek
Subramanya	2006	2, Patent Application Publication to, Pub. No.: US 2009/0275606 A1