NO135286B - - Google Patents
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- Publication number
- NO135286B NO135286B NO324070A NO324070A NO135286B NO 135286 B NO135286 B NO 135286B NO 324070 A NO324070 A NO 324070A NO 324070 A NO324070 A NO 324070A NO 135286 B NO135286 B NO 135286B
- Authority
- NO
- Norway
- Prior art keywords
- group
- methyl
- reacted
- urea
- tolylsulfonyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 70
- 239000004202 carbamide Substances 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- -1 urea compound Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 229910052727 yttrium Inorganic materials 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 8
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229960000632 dexamfetamine Drugs 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 6
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 230000003288 anthiarrhythmic effect Effects 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 claims description 3
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 239000003416 antiarrhythmic agent Substances 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 4
- VATAIZDYZPAXOX-UHFFFAOYSA-N (4-methylphenyl)sulfonylcarbamic acid Chemical compound CC1=CC=C(S(=O)(=O)NC(O)=O)C=C1 VATAIZDYZPAXOX-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 53
- 239000000243 solution Substances 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
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- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 9
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 6
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- 241000124008 Mammalia Species 0.000 description 5
- 239000000006 Nitroglycerin Substances 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 229960003711 glyceryl trinitrate Drugs 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 241000208011 Digitalis Species 0.000 description 4
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- 241001465754 Metazoa Species 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
- 229910052721 tungsten Inorganic materials 0.000 description 4
- XILWEASNBDKGSA-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-(1-phenylpropan-2-yl)urea Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)NC(=O)NC(C)CC1=CC=CC=C1 XILWEASNBDKGSA-UHFFFAOYSA-N 0.000 description 3
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- 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 2
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- 150000001342 alkaline earth metals Chemical class 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 238000009833 condensation Methods 0.000 description 2
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- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 229950010053 sulfacarbamide Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85350469A | 1969-08-27 | 1969-08-27 | |
| US87700069A | 1969-11-14 | 1969-11-14 | |
| BR21539369A BR6915393D0 (pt) | 1969-08-27 | 1969-12-19 | Processo para a preparacao de novos compostos de benzeno sulfonil-ureia |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135286B true NO135286B (pl) | 1976-12-06 |
| NO135286C NO135286C (pl) | 1977-03-16 |
Family
ID=27160209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO324070A NO135286C (pl) | 1969-08-27 | 1970-08-26 |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS4911383B1 (pl) |
| AT (1) | AT321930B (pl) |
| BE (1) | BE755382A (pl) |
| CA (1) | CA976188A (pl) |
| CH (1) | CH582136A5 (pl) |
| DE (1) | DE2042230A1 (pl) |
| ES (1) | ES383043A1 (pl) |
| FR (1) | FR2068521B1 (pl) |
| GB (1) | GB1308210A (pl) |
| IE (1) | IE35084B1 (pl) |
| IL (1) | IL35170A (pl) |
| NL (1) | NL7012544A (pl) |
| NO (1) | NO135286C (pl) |
| PL (1) | PL82799B1 (pl) |
| SE (1) | SE385582B (pl) |
| SU (1) | SU464108A3 (pl) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4579964A (en) * | 1983-03-31 | 1986-04-01 | Union Carbide Corporation | Alkoxysilyl functional silicones |
-
0
- BE BE755382D patent/BE755382A/xx unknown
-
1969
- 1969-08-27 SU SU691471980D patent/SU464108A3/ru active
-
1970
- 1970-08-25 CH CH1270970A patent/CH582136A5/xx not_active IP Right Cessation
- 1970-08-25 NL NL7012544A patent/NL7012544A/xx unknown
- 1970-08-26 NO NO324070A patent/NO135286C/no unknown
- 1970-08-26 IE IE111970A patent/IE35084B1/xx unknown
- 1970-08-26 CA CA091,692A patent/CA976188A/en not_active Expired
- 1970-08-26 GB GB4110670A patent/GB1308210A/en not_active Expired
- 1970-08-26 IL IL3517070A patent/IL35170A/xx unknown
- 1970-08-26 FR FR7031187A patent/FR2068521B1/fr not_active Expired
- 1970-08-26 ES ES383043A patent/ES383043A1/es not_active Expired
- 1970-08-26 AT AT773670A patent/AT321930B/de not_active IP Right Cessation
- 1970-08-26 SE SE1161070A patent/SE385582B/xx unknown
- 1970-08-26 PL PL14289370A patent/PL82799B1/pl unknown
- 1970-08-26 JP JP7433970A patent/JPS4911383B1/ja active Pending
- 1970-08-26 DE DE19702042230 patent/DE2042230A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AT321930B (de) | 1975-04-25 |
| PL82799B1 (en) | 1975-10-31 |
| IE35084L (en) | 1971-02-27 |
| IL35170A (en) | 1974-11-29 |
| FR2068521A1 (pl) | 1971-08-27 |
| NL7012544A (pl) | 1971-03-02 |
| IE35084B1 (en) | 1975-11-12 |
| ES383043A1 (es) | 1972-12-16 |
| JPS4911383B1 (pl) | 1974-03-16 |
| DE2042230A1 (de) | 1971-03-04 |
| NO135286C (pl) | 1977-03-16 |
| SE385582B (sv) | 1976-07-12 |
| GB1308210A (en) | 1973-02-21 |
| BE755382A (fr) | 1971-03-01 |
| SU464108A3 (ru) | 1975-03-15 |
| CH582136A5 (pl) | 1976-11-30 |
| FR2068521B1 (pl) | 1974-08-30 |
| CA976188A (en) | 1975-10-14 |
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