SU1033001A3 - Способ получени производных аминоизохинолина или их кислых солей аддитивных - Google Patents
Способ получени производных аминоизохинолина или их кислых солей аддитивных Download PDFInfo
- Publication number
- SU1033001A3 SU1033001A3 SU802905799A SU2905799A SU1033001A3 SU 1033001 A3 SU1033001 A3 SU 1033001A3 SU 802905799 A SU802905799 A SU 802905799A SU 2905799 A SU2905799 A SU 2905799A SU 1033001 A3 SU1033001 A3 SU 1033001A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- aminoisoquinoline
- addition salts
- acid addition
- methyl
- group
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 8
- 150000003839 salts Chemical class 0.000 title claims abstract description 6
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical class C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- -1 morpholino- Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 208000010513 Stupor Diseases 0.000 abstract description 2
- 125000004193 piperazinyl group Chemical group 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PSQUIUNIVDKHJK-UHFFFAOYSA-N 1-bromoisoquinolin-3-amine Chemical compound C1=CC=C2C(Br)=NC(N)=CC2=C1 PSQUIUNIVDKHJK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- HTALNGLVWLJHDB-UHFFFAOYSA-N 1-morpholin-4-ylisoquinolin-3-amine Chemical compound N=1C(N)=CC2=CC=CC=C2C=1N1CCOCC1 HTALNGLVWLJHDB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229960004815 meprobamate Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004617 sleep duration Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- AIPSCLCGQHMYLI-UHFFFAOYSA-N 1-piperidin-1-ylisoquinolin-3-amine Chemical compound N=1C(N)=CC2=CC=CC=C2C=1N1CCCCC1 AIPSCLCGQHMYLI-UHFFFAOYSA-N 0.000 description 1
- GWAURFKKLMLYII-UHFFFAOYSA-N 4-(1-morpholin-4-ylisoquinolin-3-yl)morpholine Chemical compound N1(CCOCC1)C1=NC(=CC2=CC=CC=C12)N1CCOCC1 GWAURFKKLMLYII-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 231100000570 acute poisoning Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79EE2647A HU178522B (en) | 1979-04-11 | 1979-04-11 | Process for producing amino-isoquinoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1033001A3 true SU1033001A3 (ru) | 1983-07-30 |
Family
ID=10995839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802905799A SU1033001A3 (ru) | 1979-04-11 | 1980-04-11 | Способ получени производных аминоизохинолина или их кислых солей аддитивных |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4324894A (enExample) |
| JP (1) | JPS55149261A (enExample) |
| AT (1) | AT374798B (enExample) |
| AU (1) | AU535462B2 (enExample) |
| BE (1) | BE882674A (enExample) |
| CH (1) | CH643833A5 (enExample) |
| CS (1) | CS216218B2 (enExample) |
| DD (1) | DD150055A5 (enExample) |
| DE (1) | DE3013998A1 (enExample) |
| ES (1) | ES490506A0 (enExample) |
| FR (1) | FR2453855A1 (enExample) |
| GB (1) | GB2048256B (enExample) |
| GR (1) | GR68197B (enExample) |
| HU (1) | HU178522B (enExample) |
| IT (1) | IT1148788B (enExample) |
| NL (1) | NL8002119A (enExample) |
| SU (1) | SU1033001A3 (enExample) |
| YU (1) | YU100280A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2468011C2 (ru) * | 2006-12-27 | 2012-11-27 | Санофи-Авентис | Замещенные циклоалкиламином производные изохинолина и изохинолинона |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1020445B1 (en) * | 1997-10-02 | 2008-08-13 | Eisai R&D Management Co., Ltd. | Fused pyridine derivatives |
| WO2008115593A1 (en) * | 2007-03-21 | 2008-09-25 | The University Of Montana | 1-[(2'-substituted)-piperazin-1'-yl]-isoquinolines as norepinephrine transporter inhibitor therapeutics and positron emission tomography imaging agents |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2593798A (en) * | 1947-05-22 | 1952-04-22 | Searle & Co | Aminoalkylamino isoquinoline compounds |
| CH344259A (de) * | 1955-12-21 | 1960-01-31 | Geigy Ag J R | Verfahren und Mittel zur Beeinflussung des Pflanzenwachstums |
| US3991063A (en) * | 1971-09-09 | 1976-11-09 | Wijbe Thomas Nauta | Aminoisoquinolines |
| BE788608A (fr) * | 1971-09-09 | 1973-03-08 | Koninklijke Pharma Fab Nv | Aminoisoquinoleines |
| AU465390B2 (en) | 1971-12-31 | 1975-09-10 | Ici Australia Limited | Isoquinolines |
| US3930837A (en) * | 1971-12-31 | 1976-01-06 | Ici Australia Limited | 3-chloro-5-acetamidaisoquinoline as a herbicide |
| AT342057B (de) * | 1974-04-25 | 1978-03-10 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen 3-piperazino-isochinolinen und deren salzen |
-
1979
- 1979-04-11 HU HU79EE2647A patent/HU178522B/hu not_active IP Right Cessation
-
1980
- 1980-03-31 GB GB8010793A patent/GB2048256B/en not_active Expired
- 1980-04-08 BE BE1/9778A patent/BE882674A/fr not_active IP Right Cessation
- 1980-04-10 IT IT21285/80A patent/IT1148788B/it active
- 1980-04-10 US US06/138,843 patent/US4324894A/en not_active Expired - Lifetime
- 1980-04-10 AU AU57302/80A patent/AU535462B2/en not_active Ceased
- 1980-04-10 CH CH274280A patent/CH643833A5/de not_active IP Right Cessation
- 1980-04-10 FR FR8008052A patent/FR2453855A1/fr active Granted
- 1980-04-10 DD DD80220351A patent/DD150055A5/de unknown
- 1980-04-11 JP JP4695780A patent/JPS55149261A/ja active Pending
- 1980-04-11 DE DE19803013998 patent/DE3013998A1/de not_active Withdrawn
- 1980-04-11 CS CS802538A patent/CS216218B2/cs unknown
- 1980-04-11 GR GR61658A patent/GR68197B/el unknown
- 1980-04-11 ES ES490506A patent/ES490506A0/es active Granted
- 1980-04-11 AT AT0197280A patent/AT374798B/de not_active IP Right Cessation
- 1980-04-11 YU YU01002/80A patent/YU100280A/xx unknown
- 1980-04-11 NL NL8002119A patent/NL8002119A/nl not_active Application Discontinuation
- 1980-04-11 SU SU802905799A patent/SU1033001A3/ru active
Non-Patent Citations (1)
| Title |
|---|
| 1. Бюлер К., Пирсон Д. Органические синтезы. Ч. 1. М., Мир, 1973. с. 50i. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2468011C2 (ru) * | 2006-12-27 | 2012-11-27 | Санофи-Авентис | Замещенные циклоалкиламином производные изохинолина и изохинолинона |
Also Published As
| Publication number | Publication date |
|---|---|
| AU535462B2 (en) | 1984-03-22 |
| IT8021285A0 (it) | 1980-04-10 |
| US4324894A (en) | 1982-04-13 |
| AU5730280A (en) | 1980-10-16 |
| ATA197280A (de) | 1983-10-15 |
| JPS55149261A (en) | 1980-11-20 |
| ES8103047A1 (es) | 1981-02-16 |
| FR2453855B1 (enExample) | 1983-08-26 |
| DE3013998A1 (de) | 1980-12-11 |
| DD150055A5 (de) | 1981-08-12 |
| ES490506A0 (es) | 1981-02-16 |
| CH643833A5 (de) | 1984-06-29 |
| GB2048256A (en) | 1980-12-10 |
| AT374798B (de) | 1984-05-25 |
| FR2453855A1 (fr) | 1980-11-07 |
| CS216218B2 (en) | 1982-10-29 |
| GR68197B (enExample) | 1981-11-10 |
| YU100280A (en) | 1983-10-31 |
| GB2048256B (en) | 1983-05-18 |
| NL8002119A (nl) | 1980-10-14 |
| BE882674A (fr) | 1980-10-08 |
| IT1148788B (it) | 1986-12-03 |
| HU178522B (en) | 1982-05-28 |
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