NO310868B1 - Fenyl- og aminofenyl-alkylsulfonamid og ureaderivater - Google Patents
Fenyl- og aminofenyl-alkylsulfonamid og ureaderivater Download PDFInfo
- Publication number
- NO310868B1 NO310868B1 NO19982884A NO982884A NO310868B1 NO 310868 B1 NO310868 B1 NO 310868B1 NO 19982884 A NO19982884 A NO 19982884A NO 982884 A NO982884 A NO 982884A NO 310868 B1 NO310868 B1 NO 310868B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- methanesulfonamide
- lower alkyl
- imidazol
- imidazoline
- Prior art date
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 44
- 150000003672 ureas Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 194
- 238000002360 preparation method Methods 0.000 claims description 186
- 150000003839 salts Chemical class 0.000 claims description 98
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 77
- -1 3-chloro-1-methanesulfonyl-1H-indol-6-yl Chemical group 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 68
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 38
- 238000011282 treatment Methods 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 239000003960 organic solvent Substances 0.000 claims description 27
- 229910052794 bromium Inorganic materials 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical group C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 18
- 206010028735 Nasal congestion Diseases 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical group C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 206010046543 Urinary incontinence Diseases 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 13
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- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 239000000048 adrenergic agonist Substances 0.000 claims description 9
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 238000002560 therapeutic procedure Methods 0.000 claims description 9
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 8
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
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- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical group Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 6
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- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 6
- AREIITMVZLHETP-UHFFFAOYSA-N 2-[[3-(dimethylsulfamoylamino)phenoxy]methyl]-4,5-dihydro-1h-imidazole;hydrochloride Chemical compound Cl.CN(C)S(=O)(=O)NC1=CC=CC(OCC=2NCCN=2)=C1 AREIITMVZLHETP-UHFFFAOYSA-N 0.000 claims description 5
- BFYRXCWLDJORHM-UHFFFAOYSA-N 2-chloro-4,5-dihydro-1h-imidazole Chemical compound ClC1=NCCN1 BFYRXCWLDJORHM-UHFFFAOYSA-N 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
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- 239000011698 potassium fluoride Substances 0.000 claims description 4
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- XTYYJCFSNYXYGV-UHFFFAOYSA-N n-[3-(4,5-dihydro-1h-imidazol-2-ylmethyl)-2-methylphenyl]methanesulfonamide Chemical compound C1=CC=C(NS(C)(=O)=O)C(C)=C1CC1=NCCN1 XTYYJCFSNYXYGV-UHFFFAOYSA-N 0.000 claims description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 83
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
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- Neurosurgery (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
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- Obesity (AREA)
- Diabetes (AREA)
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- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Otolaryngology (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
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Applications Claiming Priority (2)
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US5047997P | 1997-06-23 | 1997-06-23 | |
US7597898P | 1998-02-25 | 1998-02-25 |
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NO982884D0 NO982884D0 (no) | 1998-06-19 |
NO982884L NO982884L (no) | 1998-12-28 |
NO310868B1 true NO310868B1 (no) | 2001-09-10 |
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NO19982884A NO310868B1 (no) | 1997-06-23 | 1998-06-19 | Fenyl- og aminofenyl-alkylsulfonamid og ureaderivater |
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EP (1) | EP0887346B1 (id) |
JP (1) | JP2977536B2 (id) |
KR (1) | KR100608501B1 (id) |
CN (3) | CN1262547C (id) |
AR (1) | AR013005A1 (id) |
AT (1) | ATE380793T1 (id) |
AU (1) | AU713068C (id) |
BR (1) | BR9802201B1 (id) |
CA (3) | CA2240136C (id) |
CO (1) | CO4940479A1 (id) |
CZ (1) | CZ197498A3 (id) |
DE (1) | DE69838829T2 (id) |
ES (1) | ES2297870T3 (id) |
HK (1) | HK1016985A1 (id) |
HR (1) | HRP980353A2 (id) |
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ID (1) | ID20463A (id) |
IL (2) | IL124839A (id) |
MA (1) | MA26515A1 (id) |
MY (1) | MY128048A (id) |
NO (1) | NO310868B1 (id) |
NZ (1) | NZ330506A (id) |
PE (1) | PE85999A1 (id) |
PL (1) | PL198053B1 (id) |
RU (1) | RU2218335C2 (id) |
SG (1) | SG72827A1 (id) |
TR (1) | TR199801197A2 (id) |
TW (1) | TW517049B (id) |
UY (1) | UY25057A1 (id) |
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WO2009012283A1 (en) | 2007-07-17 | 2009-01-22 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
KR20100096262A (ko) * | 2008-02-04 | 2010-09-01 | 에프. 호프만-라 로슈 아게 | 신규한 이미다졸리닐메틸 아릴 설폰아미드 |
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JP4168086B1 (ja) * | 2008-04-16 | 2008-10-22 | 国立大学法人福井大学 | イミダゾリン誘導体 |
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US8329724B2 (en) | 2009-08-03 | 2012-12-11 | Hoffmann-La Roche Inc. | Process for the manufacture of pharmaceutically active compounds |
ES2633317T3 (es) | 2009-11-06 | 2017-09-20 | Plexxikon, Inc. | Compuestos y métodos para la modulación de quinasas, e indicaciones para ello |
PT2672967T (pt) | 2011-02-07 | 2018-12-07 | Plexxikon Inc | Compostos e métodos de modulação da quinase e suas indicações |
AR085279A1 (es) | 2011-02-21 | 2013-09-18 | Plexxikon Inc | Formas solidas de {3-[5-(4-cloro-fenil)-1h-pirrolo[2,3-b]piridina-3-carbonil]-2,4-difluor-fenil}-amida del acido propano-1-sulfonico |
US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
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CN106543077B (zh) * | 2016-10-27 | 2019-08-23 | 西安交通大学 | N,n’-双取代芳基硫脲衍生物及其合成方法和应用 |
CN106905181B (zh) * | 2017-04-14 | 2018-10-09 | 上海海洋大学 | 一种立达霉代谢产物16的合成方法 |
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-
1998
- 1998-05-18 SG SG1998001348A patent/SG72827A1/en unknown
- 1998-05-25 NZ NZ330506A patent/NZ330506A/xx unknown
- 1998-06-03 US US09/089,779 patent/US5952362A/en not_active Expired - Lifetime
- 1998-06-05 CA CA002240136A patent/CA2240136C/en not_active Expired - Fee Related
- 1998-06-05 CA CA002418778A patent/CA2418778C/en not_active Expired - Fee Related
- 1998-06-05 CA CA002430623A patent/CA2430623A1/en not_active Abandoned
- 1998-06-10 IL IL12483998A patent/IL124839A/en not_active IP Right Cessation
- 1998-06-12 ID IDP980873A patent/ID20463A/id unknown
- 1998-06-12 ES ES98110822T patent/ES2297870T3/es not_active Expired - Lifetime
- 1998-06-12 EP EP98110822A patent/EP0887346B1/en not_active Expired - Lifetime
- 1998-06-12 AT AT98110822T patent/ATE380793T1/de active
- 1998-06-12 DE DE69838829T patent/DE69838829T2/de not_active Expired - Lifetime
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- 1998-06-19 JP JP10172403A patent/JP2977536B2/ja not_active Expired - Fee Related
- 1998-06-19 AR ARP980102929A patent/AR013005A1/es not_active Application Discontinuation
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- 1998-06-19 UY UY25057A patent/UY25057A1/es unknown
- 1998-06-22 PE PE1998000547A patent/PE85999A1/es not_active Application Discontinuation
- 1998-06-22 RU RU98111769/04A patent/RU2218335C2/ru not_active IP Right Cessation
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- 1998-06-22 MA MA25130A patent/MA26515A1/fr unknown
- 1998-06-22 CN CNB031386059A patent/CN1262547C/zh not_active Expired - Fee Related
- 1998-06-22 CN CNA031264069A patent/CN1515559A/zh active Pending
- 1998-06-22 CN CNB981152090A patent/CN1176910C/zh not_active Expired - Fee Related
- 1998-06-22 CZ CZ981974A patent/CZ197498A3/cs unknown
- 1998-06-22 PL PL326959A patent/PL198053B1/pl not_active IP Right Cessation
- 1998-06-22 AU AU73102/98A patent/AU713068C/en not_active Ceased
- 1998-06-23 TR TR1998/01197A patent/TR199801197A2/xx unknown
- 1998-06-23 BR BRPI9802201-6A patent/BR9802201B1/pt not_active IP Right Cessation
- 1998-06-23 HR HR60/075,978A patent/HRP980353A2/hr not_active Application Discontinuation
- 1998-06-23 TW TW087110098A patent/TW517049B/zh not_active IP Right Cessation
-
1999
- 1999-03-08 US US09/264,467 patent/US6057349A/en not_active Expired - Fee Related
- 1999-05-24 HK HK99102263A patent/HK1016985A1/xx not_active IP Right Cessation
-
2003
- 2003-09-04 IL IL15774503A patent/IL157745A0/xx unknown
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