CS357891A3 - /2-(dimethylamino)ethyl/-/2-//2-(methylthio)phenyl/amino/-2-oxoethyl/carbamates or ureas thereof, process oftheir preparation and pharmaceutical compositions containing said carbamates orureas - Google Patents

/2-(dimethylamino)ethyl/-/2-//2-(methylthio)phenyl/amino/-2-oxoethyl/carbamates or ureas thereof, process oftheir preparation and pharmaceutical compositions containing said carbamates orureas Download PDF

Info

Publication number: CS357891A3
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; carbamates; phenyl; methylthio
Prior art date: 1986-07-08

Application number

CS913578A

Other languages

Czech (cs)

English (en)

Inventor

Nigel Beeley

Gerard Cremer

Original Assignee

Synthelabo

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.)

1986-07-08

Filing date

1991-11-25

Publication date

1992-12-16

1991-11-25 Application filed by Synthelabo filed Critical Synthelabo

1992-12-16 Publication of CS357891A3 publication Critical patent/CS357891A3/cs

Links

238000002360 preparation method Methods 0.000 title claims description 9
238000000034 method Methods 0.000 title claims description 4
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
230000008569 process Effects 0.000 title claims description 3
150000003672 ureas Chemical class 0.000 title abstract description 4
150000004657 carbamic acid derivatives Chemical class 0.000 title description 5
235000013877 carbamide Nutrition 0.000 title description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 41
150000001875 compounds Chemical class 0.000 claims abstract description 26
-1 methylenedioxy group Chemical group 0.000 claims abstract description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
125000005843 halogen group Chemical group 0.000 claims abstract description 10
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
239000002253 acid Substances 0.000 claims abstract description 4
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000005605 benzo group Chemical group 0.000 claims abstract description 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
239000001257 hydrogen Substances 0.000 claims abstract 3
229910052736 halogen Inorganic materials 0.000 claims abstract 2
150000002367 halogens Chemical group 0.000 claims abstract 2
238000006243 chemical reaction Methods 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
WBRPQQSADOCKCH-UHFFFAOYSA-N 2-methylsulfanylaniline Chemical compound CSC1=CC=CC=C1N WBRPQQSADOCKCH-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000002466 imines Chemical class 0.000 claims description 3
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 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
150000004985 diamines Chemical class 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
229940127291 Calcium channel antagonist Drugs 0.000 abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
150000002431 hydrogen Chemical group 0.000 abstract 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
239000000480 calcium channel blocker Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002904 solvent Substances 0.000 description 8
239000002585 base Substances 0.000 description 7
230000008602 contraction Effects 0.000 description 7
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000011575 calcium Substances 0.000 description 6
229910052791 calcium Inorganic materials 0.000 description 6
239000000203 mixture Substances 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
244000025254 Cannabis sativa Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
210000000709 aorta Anatomy 0.000 description 3
230000009989 contractile response Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
229960001789 papaverine Drugs 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
229960003712 propranolol Drugs 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
208000031229 Cardiomyopathies Diseases 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
206010061216 Infarction Diseases 0.000 description 1
206010026749 Mania Diseases 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
208000006011 Stroke Diseases 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000000767 anti-ulcer Effects 0.000 description 1
210000002376 aorta thoracic Anatomy 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000002999 depolarising effect Effects 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
230000035622 drinking Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000007574 infarction Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000013178 mathematical model Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
YXMXAXHPRPWBJB-UHFFFAOYSA-N n-phenoxy-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CNOC1=CC=CC=C1 YXMXAXHPRPWBJB-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000003826 tablet Substances 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
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000002792 vascular Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/41—Y being a hydrogen or an acyclic carbon atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hematology (AREA)
Obesity (AREA)
Diabetes (AREA)
Emergency Medicine (AREA)
Rheumatology (AREA)
Endocrinology (AREA)
Epidemiology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Medicinal Preparation (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CS913578A 1986-07-08 1991-11-25 /2-(dimethylamino)ethyl/-/2-//2-(methylthio)phenyl/amino/-2-oxoethyl/carbamates or ureas thereof, process oftheir preparation and pharmaceutical compositions containing said carbamates orureas CS357891A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8609887A FR2601363B1 (fr)	1986-07-08	1986-07-08	(dimethylamino)-2 ethyl) ((((methylthio)-2 phenyl) (phenylmethyl)amino)-2 oxo-2 ethyl) carbamates ou urees, leur preparation et leur application en therapeutique.

Publications (1)

Publication Number	Publication Date
CS357891A3 true CS357891A3 (en)	1992-12-16

Family

ID=9337176

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS913578A CS357891A3 (en)	1986-07-08	1991-11-25	/2-(dimethylamino)ethyl/-/2-//2-(methylthio)phenyl/amino/-2-oxoethyl/carbamates or ureas thereof, process oftheir preparation and pharmaceutical compositions containing said carbamates orureas

Country Status (19)

Country	Link
US (1)	US4840967A (de)
EP (1)	EP0252810B1 (de)
JP (1)	JPS6323856A (de)
KR (1)	KR880001587A (de)
AT (1)	ATE62669T1 (de)
AU (1)	AU595340B2 (de)
CA (1)	CA1277330C (de)
CS (1)	CS357891A3 (de)
DE (1)	DE3769384D1 (de)
DK (1)	DK349287A (de)
FI (1)	FI85583C (de)
FR (1)	FR2601363B1 (de)
GR (1)	GR3002081T3 (de)
HU (1)	HU196169B (de)
IL (1)	IL83092A (de)
NO (1)	NO164593C (de)
NZ (1)	NZ220987A (de)
PT (1)	PT85280B (de)
ZA (1)	ZA874945B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2641279B1 (fr) *	1989-01-03	1991-02-22	Synthelabo	Derives de n-(amino-2 ethyl) n-(((methylthio-2 phenyl) (phenylmethyl)amino)-2 oxo ethyl)amides et carbamates, leur preparation et leur application en therapeutique
JPH02290464A (ja) *	1989-04-28	1990-11-30	Takagi Ind Co Ltd	瞬間湯沸器
EP0903341A1 (de) *	1997-07-22	1999-03-24	Akzo Nobel N.V.	Ortho-Mercaptoanilinverbindungen
US6221913B1 (en) *	1998-01-21	2001-04-24	Zymogenetics, Inc.	Dialkyl ureas as calcitonin mimetics
CN1610659A (zh) *	2001-12-27	2005-04-27	大正制药株式会社	羧酸衍生物
FR2885129B1 (fr) *	2005-04-29	2007-06-15	Proskelia Sas	Nouveaux derives de l'ureee substituee parun thiazole ou benzothiazole, leur procede de preparation, leur application a titre de medicaments, les compositions pharmaceutiques les renfermant et utilisation.
JP2010512417A (ja) *	2006-12-11	2010-04-22	ワイスエルエルシー	イオンチャネルモジュレータ−
RU2517190C2 (ru) *	2008-08-13	2014-05-27	Внтрисерч Аб	Применение производных пептида wnt5-a для лечения меланомы и рака желудка
EP2726880B1 (de)	2011-07-01	2019-04-17	Wntresearch AB	Behandlung von prostatakrebs und verfahren zur bestimmung der prognose von prostatakrebspatienten
ES2993327T3 (en) *	2014-08-06	2024-12-27	Ascendis Pharma As	Prodrugs comprising an aminoalkyl glycine linker

1986
- 1986-07-08 FR FR8609887A patent/FR2601363B1/fr not_active Expired
1987
- 1987-07-01 DE DE8787401523T patent/DE3769384D1/de not_active Expired - Fee Related
- 1987-07-01 EP EP87401523A patent/EP0252810B1/de not_active Expired - Lifetime
- 1987-07-01 AT AT87401523T patent/ATE62669T1/de not_active IP Right Cessation
- 1987-07-06 IL IL83092A patent/IL83092A/xx unknown
- 1987-07-07 JP JP62169610A patent/JPS6323856A/ja active Pending
- 1987-07-07 US US07/070,580 patent/US4840967A/en not_active Expired - Fee Related
- 1987-07-07 HU HU873054A patent/HU196169B/hu unknown
- 1987-07-07 FI FI873009A patent/FI85583C/fi not_active IP Right Cessation
- 1987-07-07 PT PT85280A patent/PT85280B/pt not_active IP Right Cessation
- 1987-07-07 KR KR1019870007251A patent/KR880001587A/ko not_active Withdrawn
- 1987-07-07 AU AU75294/87A patent/AU595340B2/en not_active Ceased
- 1987-07-07 NZ NZ220987A patent/NZ220987A/xx unknown
- 1987-07-07 ZA ZA874945A patent/ZA874945B/xx unknown
- 1987-07-07 DK DK349287A patent/DK349287A/da not_active Application Discontinuation
- 1987-07-07 CA CA000541475A patent/CA1277330C/en not_active Expired - Fee Related
- 1987-07-07 NO NO872832A patent/NO164593C/no unknown
1991
- 1991-06-06 GR GR91400752T patent/GR3002081T3/el unknown
- 1991-11-25 CS CS913578A patent/CS357891A3/cs unknown

Also Published As

Publication number	Publication date
FR2601363B1 (fr)	1988-10-21
EP0252810B1 (de)	1991-04-17
PT85280B (pt)	1990-03-30
NO872832D0 (no)	1987-07-07
PT85280A (fr)	1987-08-01
US4840967A (en)	1989-06-20
NZ220987A (en)	1989-12-21
FI873009A7 (fi)	1988-01-09
DE3769384D1 (de)	1991-05-23
EP0252810A3 (en)	1988-09-07
FR2601363A1 (fr)	1988-01-15
NO164593B (no)	1990-07-16
AU595340B2 (en)	1990-03-29
HUT44482A (en)	1988-03-28
FI85583C (fi)	1992-05-11
ZA874945B (en)	1988-02-24
NO872832L (no)	1988-01-11
ATE62669T1 (de)	1991-05-15
IL83092A0 (en)	1987-12-31
DK349287D0 (da)	1987-07-07
FI85583B (fi)	1992-01-31
EP0252810A2 (de)	1988-01-13
GR3002081T3 (en)	1992-12-30
JPS6323856A (ja)	1988-02-01
DK349287A (da)	1988-01-09
FI873009A0 (fi)	1987-07-07
HU196169B (en)	1988-10-28
AU7529487A (en)	1988-01-14
NO164593C (no)	1990-10-24
KR880001587A (ko)	1988-04-25
IL83092A (en)	1991-11-21
CA1277330C (en)	1990-12-04

Publication	Publication Date	Title
EP1078925A1 (de)	2001-02-28	4-Phenylpiperidin-Derivate
DK170332B1 (da)	1995-08-07	Farmakologisk aktive substituerede benzamider, fremgangsmåde til fremstilling deraf og et farmaceutisk præparat heraf
US4980365A (en)	1990-12-25	N-substituted-5,6-dimethoxy-1,2-benzisoxazole-3-propanamine and related compounds as analgesic and hypotensive agents
DK148688B (da)	1985-09-02	Analogifremgangsmaade til fremstilling af basisk substituerede 7-alkylteofyllinderivater eller salte deraf med farmaceutisk acceptable syrer
US3974158A (en)	1976-08-10	2-(Substituted anilino)methylmorpholines
BG61260B1 (en)	1997-04-30	Orthosubstituted biphenyl amidine and biphenyl guanidinederivatives and antidiabetic or hypoglycamic agents containingthem
DK163181B (da)	1992-02-03	Analogifremgangsmaade til fremstilling af n,n'-di(arylalkylen)alkylendiaminer eller farmaceutisk acceptable salte deraf
AU595340B2 (en)	1990-03-29	Carbamate or urea derivatives, their preparation and pharmaceutical compositions comprising them
FI80448C (fi)	1990-06-11	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara piperazinkarboxamidderivat.
PL128505B1 (en)	1984-02-29	Process for preparing novel 2-/4-(diphenylmethylene)-1-piperidinyl/-acetic acids
US6667309B2 (en)	2003-12-23	Cyclobutene derivatives useful as antagonists of the motilin receptor
GB2142021A (en)	1985-01-09	1 4-dihydropyridine derivatives their preparation and pharmaceutical compositions containing them
JP2661892B2 (ja)	1997-10-08	Ｎ−アリールアルキルフェニルアセトアミド化合物
US4528375A (en)	1985-07-09	Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity
KR880002209B1 (ko)	1988-10-18	치환된 3,4-디아미노-1,2,5-티아디아졸류 및 그의 제조방법
JPH0317083A (ja)	1991-01-25	置換チエノピリミジン誘導体
US4600779A (en)	1986-07-15	Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity
US4528378A (en)	1985-07-09	Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity
IE59660B1 (en)	1994-03-09	Quinoline derivatives
US4528377A (en)	1985-07-09	Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity
KR20000005465A (ko)	2000-01-25	N-아미노알킬-2-안트라퀴논카르복스아미드;신규한도파민수용체서브타입특이적리간드
US4588826A (en)	1986-05-13	Ethanediimidamide intermediates
EP0167245A1 (de)	1986-01-08	Antiarrhythmische Mittel
DK170972B1 (da)	1996-04-09	(+)-1-[(3,4,5-Trimethoxy)benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylamin samt lægemidler med indhold af denne forbindelse
US4578471A (en)	1986-03-25	Substituted amino alkyl pyridyl ethanediimidamides