NO800720L - Ureaderivater. - Google Patents

Ureaderivater.

Info

Publication number: NO800720L
Authority: NO; Norway
Prior art keywords: isocyanatothiophene; thienyl; urea; creatinine; formula
Prior art date: 1979-03-14

Application number

NO800720A

Other languages

English (en)

Norwegian (no)

Inventor

Walter Hunkeler

Emilio Kyburz

Original Assignee

Hoffmann La Roche

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.)

1979-03-14

Filing date

1980-03-13

Publication date

1980-09-15

1980-03-13 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1980-09-15 Publication of NO800720L publication Critical patent/NO800720L/no

Links

XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 5
DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 claims description 18
150000003672 ureas Chemical class 0.000 claims description 11
230000000949 anxiolytic effect Effects 0.000 claims description 9
229940109239 creatinine Drugs 0.000 claims description 9
QVLWPBIUVXZGRK-UHFFFAOYSA-N 2-isocyanatothiophene Chemical compound O=C=NC1=CC=CS1 QVLWPBIUVXZGRK-UHFFFAOYSA-N 0.000 claims description 7
PVIZQOWWCLBJES-UHFFFAOYSA-N 3-isocyanatothiophene Chemical compound O=C=NC=1C=CSC=1 PVIZQOWWCLBJES-UHFFFAOYSA-N 0.000 claims description 7
239000002249 anxiolytic agent Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
229940005530 anxiolytics Drugs 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
MJFRKRPQCDIYEO-UHFFFAOYSA-N 2-chloro-4-isocyanatothiophene Chemical compound ClC1=CC(N=C=O)=CS1 MJFRKRPQCDIYEO-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000012360 testing method Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
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 7
239000000203 mixture Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
-1 1-(1-methyl-4-oxo-2-imidazolin-2-yl)-3-thienyl-urea derivatives Chemical class 0.000 description 6
229920002261 Corn starch Polymers 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
239000008120 corn starch Substances 0.000 description 6
229940099112 cornstarch Drugs 0.000 description 6
230000035939 shock Effects 0.000 description 6
241000700159 Rattus Species 0.000 description 5
239000007903 gelatin capsule Substances 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
239000006187 pill Substances 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000008187 granular material Substances 0.000 description 4
229920005862 polyol Polymers 0.000 description 4
150000003077 polyols Chemical class 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000829 suppository Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000008298 dragée Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000001993 wax Substances 0.000 description 3
HMVUJESUGTZTAI-UHFFFAOYSA-N 1-(3-methyl-5-oxo-4h-imidazol-2-yl)-3-thiophen-3-ylurea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CSC=C1 HMVUJESUGTZTAI-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000010171 animal model Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000003925 fat Substances 0.000 description 2
235000019197 fats Nutrition 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 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
239000000155 melt Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000003158 myorelaxant agent Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
238000002203 pretreatment Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
230000007017 scission Effects 0.000 description 2
230000001624 sedative effect Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 2
239000012485 toluene extract Substances 0.000 description 2
239000002966 varnish Substances 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
CJVARLRPLSTDEB-UHFFFAOYSA-N 1-(3-methyl-5-oxo-4h-imidazol-2-yl)-3-thiophen-2-ylurea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=CS1 CJVARLRPLSTDEB-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
POVPYUUZOZBLOH-UHFFFAOYSA-N 5-chlorothiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC(Cl)=C1 POVPYUUZOZBLOH-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
241000699670 Mus sp. Species 0.000 description 1
PSEQILAVBVITPG-UHFFFAOYSA-N N=C=O.C=1C=CSC=1 Chemical compound N=C=O.C=1C=CSC=1 PSEQILAVBVITPG-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229910000831 Steel Inorganic materials 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
229930006000 Sucrose Natural products 0.000 description 1
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
238000001793 Wilcoxon signed-rank test Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000004203 carnauba wax Substances 0.000 description 1
235000013869 carnauba wax Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229960004782 chlordiazepoxide Drugs 0.000 description 1
ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
239000008011 inorganic excipient Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 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
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000008012 organic excipient Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008137 solubility enhancer Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
QTWBEVAYYDZLQL-UHFFFAOYSA-N thiophene-3-carbonyl chloride Chemical compound ClC(=O)C=1C=CSC=1 QTWBEVAYYDZLQL-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- C07D333/36—Nitrogen 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

NO800720A 1979-03-14 1980-03-13 Ureaderivater. NO800720L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH241579		1979-03-14
CH17180		1980-01-10

Publications (1)

Publication Number	Publication Date
NO800720L true NO800720L (no)	1980-09-15

Family

ID=25683737

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO800720A NO800720L (no)	1979-03-14	1980-03-13	Ureaderivater.

Country Status (10)

Country	Link
EP (1)	EP0016371A1 (da)
AU (1)	AU5628380A (da)
DK (1)	DK108780A (da)
ES (1)	ES489493A0 (da)
FI (1)	FI800559A7 (da)
GR (1)	GR66630B (da)
IL (1)	IL59563A0 (da)
MC (1)	MC1317A1 (da)
NO (1)	NO800720L (da)
PT (1)	PT70949B (da)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7517880B2 (en)	1997-12-22	2009-04-14	Bayer Pharmaceuticals Corporation	Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas
US7329670B1 (en)	1997-12-22	2008-02-12	Bayer Pharmaceuticals Corporation	Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas
US8124630B2 (en)	1999-01-13	2012-02-28	Bayer Healthcare Llc	ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US7351834B1 (en)	1999-01-13	2008-04-01	Bayer Pharmaceuticals Corporation	ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
EP1140840B1 (en)	1999-01-13	2006-03-22	Bayer Pharmaceuticals Corp.	-g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US7928239B2 (en)	1999-01-13	2011-04-19	Bayer Healthcare Llc	Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas
EP2298311B1 (en)	1999-01-13	2012-05-09	Bayer HealthCare LLC	w-Carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors
US7235576B1 (en)	2001-01-12	2007-06-26	Bayer Pharmaceuticals Corporation	Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
US7371763B2 (en)	2001-04-20	2008-05-13	Bayer Pharmaceuticals Corporation	Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas
WO2003068229A1 (en)	2002-02-11	2003-08-21	Bayer Pharmaceuticals Corporation	Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors
ATE529406T1 (de)	2002-02-11	2011-11-15	Bayer Healthcare Llc	Aryl-harnstoffe als kinase inhibitoren
DK1478358T3 (da)	2002-02-11	2013-10-07	Bayer Healthcare Llc	Sorafenibtosylat til behandling af sygdomme kendetegnet ved unormal angiogenese
UY28213A1 (es)	2003-02-28	2004-09-30	Bayer Pharmaceuticals Corp	Nuevos derivados de cianopiridina útiles en el tratamiento de cáncer y otros trastornos.
EP1636585B2 (en)	2003-05-20	2012-06-13	Bayer HealthCare LLC	Diaryl ureas with kinase inhibiting activity
PL1663978T3 (pl)	2003-07-23	2008-04-30	Bayer Healthcare Llc	Fluoropodstawiony omega-karboksyarylodifenylomocznik do leczenia i profilaktyki chorób i stanów
US7838524B2 (en)	2004-04-30	2010-11-23	Bayer Healthcare Llc	Substituted pyrazolyl urea derivatives useful in the treatment of cancer

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2448869A1 (de) *	1973-10-19	1975-09-04	Mcneilab Inc	4-oxo-2-imidazolidinylidenharnstoffe, verfahren zu ihrer herstellung und arzneimittel
US3983135A (en) *	1974-09-23	1976-09-28	Mcneil Laboratories, Incorporated	4-Oxo-2-imidazolidinylidene ureas
US4025517A (en) *	1975-06-23	1977-05-24	Mcneil Laboratories, Incorporated	4-Oxo-2-hexahydropyrimidinylidene ureas

1980
- 1980-02-26 FI FI800559A patent/FI800559A7/fi not_active Application Discontinuation
- 1980-03-05 EP EP80101097A patent/EP0016371A1/de not_active Withdrawn
- 1980-03-07 AU AU56283/80A patent/AU5628380A/en not_active Abandoned
- 1980-03-10 IL IL59563A patent/IL59563A0/xx unknown
- 1980-03-11 GR GR61403A patent/GR66630B/el unknown
- 1980-03-13 ES ES489493A patent/ES489493A0/es active Granted
- 1980-03-13 PT PT70949A patent/PT70949B/pt unknown
- 1980-03-13 NO NO800720A patent/NO800720L/no unknown
- 1980-03-13 DK DK108780A patent/DK108780A/da unknown
- 1980-03-14 MC MC801437A patent/MC1317A1/fr unknown

Also Published As

Publication number	Publication date
GR66630B (da)	1981-04-03
EP0016371A1 (de)	1980-10-01
ES8103737A1 (es)	1981-03-16
FI800559A7 (fi)	1981-01-01
PT70949A (en)	1980-04-01
AU5628380A (en)	1980-09-18
DK108780A (da)	1980-09-15
MC1317A1 (fr)	1981-03-10
IL59563A0 (en)	1980-06-30
ES489493A0 (es)	1981-03-16
PT70949B (en)	1981-06-24

Publication	Publication Date	Title
DK167573B1 (da)	1993-11-22	Faste former af 2-ethoxy-4-oen-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethylaa-benzoesyre, laegemidler indeholdende disse former, fremgangsmaade til fremstilling af de faste former, samt fremgangsmaade til fremstilling af et laegemiddel
EP0059391B1 (de)	1985-05-08	Imidazodiazepine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
EP0147768A2 (de)	1985-07-10	Glycerinderivate
NO154883B (no)	1986-09-29	Analogifremgangsmaate ved fremstilling av nye, terapeutisk aktive 2-acylaminomethyl-1,4-benzodiazepiner.
DE3131752C2 (da)	1992-04-23
BG64622B1 (bg)	2005-09-30	2-(3,5-бис-трифлуорометил-фенил)-n-метил-n-(6-морфолин-4-ил)-4-о-толил-пиридин-3-ил)-изобутирамид, метод за получаване и използването му
JPS6061595A (ja)	1985-04-09	ステロイド
EP0016371A1 (de)	1980-10-01	Neue Harnstoffderivate, Verfahren und Zwischenprodukte zu deren Herstellung und Arzneimittel enthaltend ein solches Harnstoffderivat sowie die Verwendung eines solchen Harnstoffderivates bei der Bekämpfung von Krankheiten
US4330472A (en)	1982-05-18	Meta-sulfonamido-benzamide derivatives
EP0387618B1 (de)	1994-07-27	1,7-anellierte 1H-Indol-2-carbonsäure-N-(1,4-benzodiazepin-3-yl)amide
NO161619B (no)	1989-05-29	Analogifremgangsmaate for fremstilling av terapeutisk aktive substituerte 5,11-dihydro-6-dibenz(b,e)-azepin-6-on-derivater.
HU185422B (en)	1985-02-28	Process for producing phenyl-azacycloalkanes
EP1392679B1 (de)	2005-11-02	Neue 1-amidomethylcarbonyl-piperidinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
JPS5959685A (ja)	1984-04-05	新規なピペリジン誘導体
EP0170861B1 (de)	1988-03-09	3-Aminocarbonylmethoxy-5-phenylpyrazol-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE69724941T2 (de)	2004-07-15	Aminopyridin-derivate
NO158623B (no)	1988-07-04	Analogifremgangsm te for fremstilling av terapeutisk aktive dibenzodiazepinon derivater.
US4391978A (en)	1983-07-05	Phenyl-quinolizidines
IE43780B1 (en)	1981-05-20	Piperidinoalkyl derivatives of purines
EP0042354B1 (de)	1985-12-11	Imidazobenzothiadiazepine, Verfahren zu ihrer Herstellung sowie pharmazeutische Präparate die diese Verbindungen enthalten
EP0072029B1 (de)	1986-10-22	Triazolobenzazepine, Verfahren und Zwischenprodukte zu deren Herstellung und diese enthaltende Arzneimittel
EP0008421B1 (de)	1984-02-08	Benzodiazepin-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
NO158736B (no)	1988-07-18	Analogifremgangsmaate for fremstilling av tetrahydropyridinderivater.
DE69705032T2 (de)	2001-11-22	Heterocyclyl-ergolinderivate als 5-ht1a rezeptor liganden
DK159679B (da)	1990-11-19	Analogifremgangsmaade til fremstilling af hydroxyderivater af 1-(p-methoxybenzoyl)-2-pyrrolidon samt beskyttede hydroxyderivater af 1-(p-methoxybenzoyl)-2-pyrrolidon til anvendelse ved fremgangsmaaden