DE60209149T2 - Industriell anwendbares verfahren zur sulfamoylation von alkoholen und von phenolen - Google Patents
Industriell anwendbares verfahren zur sulfamoylation von alkoholen und von phenolen Download PDFInfo
- Publication number
- DE60209149T2 DE60209149T2 DE60209149T DE60209149T DE60209149T2 DE 60209149 T2 DE60209149 T2 DE 60209149T2 DE 60209149 T DE60209149 T DE 60209149T DE 60209149 T DE60209149 T DE 60209149T DE 60209149 T2 DE60209149 T2 DE 60209149T2
- Authority
- DE
- Germany
- Prior art keywords
- trien
- sulfamoyl chloride
- ylsulfamate
- formic acid
- catalyst
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000005849 sulfamoylation reaction Methods 0.000 title abstract description 9
- 150000001298 alcohols Chemical class 0.000 title abstract description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 24
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 claims abstract description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 14
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims abstract description 13
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 235000019253 formic acid Nutrition 0.000 claims abstract description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000009825 accumulation Methods 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- URHINZFGVBMXAX-CBZIJGRNSA-N [(8r,9s,13s,14s)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-yl]sulfamic acid Chemical compound OS(=O)(=O)NC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 URHINZFGVBMXAX-CBZIJGRNSA-N 0.000 claims description 7
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims description 6
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims description 6
- 229960003399 estrone Drugs 0.000 claims description 6
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 12
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract description 5
- 150000002989 phenols Chemical class 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 2
- 231100001261 hazardous Toxicity 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- -1 steroid sulfamates Chemical class 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 1
- BKOHBHRABNPXGE-BDXSIMOUSA-N C1CC2=CC(NS(O)(=O)=O)=CC=C2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 Chemical class C1CC2=CC(NS(O)(=O)=O)=CC=C2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 BKOHBHRABNPXGE-BDXSIMOUSA-N 0.000 description 1
- 101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 1
- 241001282153 Scopelogadus mizolepis Species 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000003367 polycyclic group Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 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 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
- C01B21/093—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more sulfur atoms
- C01B21/096—Amidosulfonic acid; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0072—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the A ring of the steroid being aromatic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34187701P | 2001-12-21 | 2001-12-21 | |
| US341877P | 2001-12-21 | ||
| PCT/EP2002/014487 WO2003053992A2 (en) | 2001-12-21 | 2002-12-18 | Industrially applicable process for the sulfamoylation of alcohols and phenols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60209149D1 DE60209149D1 (de) | 2006-04-20 |
| DE60209149T2 true DE60209149T2 (de) | 2006-10-19 |
Family
ID=23339393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60209149T Expired - Lifetime DE60209149T2 (de) | 2001-12-21 | 2002-12-18 | Industriell anwendbares verfahren zur sulfamoylation von alkoholen und von phenolen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7067683B2 (https=) |
| EP (1) | EP1456224B1 (https=) |
| JP (1) | JP4347696B2 (https=) |
| AT (1) | ATE317369T1 (https=) |
| AU (1) | AU2002358755A1 (https=) |
| DE (1) | DE60209149T2 (https=) |
| DK (1) | DK1456224T3 (https=) |
| ES (1) | ES2256576T3 (https=) |
| PT (1) | PT1456224E (https=) |
| WO (1) | WO2003053992A2 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE317369T1 (de) | 2001-12-21 | 2006-02-15 | Schering Ag | Industriell anwendbares verfahren zur sulfamoylation von alkoholen und von phenolen |
| EP2178880B1 (en) | 2007-08-02 | 2017-10-04 | Millennium Pharmaceuticals, Inc. | Process for the synthesis of e1 activating enzyme inhibitors |
| KR101577159B1 (ko) | 2008-07-31 | 2015-12-11 | 세노믹스, 인코포레이티드 | 단맛 향상제의 제조 방법 및 중간체 |
| JP7453210B2 (ja) | 2018-08-07 | 2024-03-19 | フィルメニッヒ インコーポレイテッド | ５－置換４－アミノ－１Ｈ－ベンゾ［ｃ］［１，２，６］チアジアジン２，２－ジオキシド並びにその配合物及び使用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT94305B (pt) * | 1989-06-12 | 1997-02-28 | Robins Co Inc A H | Processo para a preparacao de compostos tendo um ou mais radicais aminossulfoniloxi uteis como produtos farmaceuticos |
| AU783910B2 (en) * | 1999-04-30 | 2005-12-22 | Sterix Limited | Use of estrone derivatives as antitumour agents |
| ATE317369T1 (de) | 2001-12-21 | 2006-02-15 | Schering Ag | Industriell anwendbares verfahren zur sulfamoylation von alkoholen und von phenolen |
-
2002
- 2002-12-18 AT AT02793067T patent/ATE317369T1/de active
- 2002-12-18 ES ES02793067T patent/ES2256576T3/es not_active Expired - Lifetime
- 2002-12-18 EP EP02793067A patent/EP1456224B1/en not_active Expired - Lifetime
- 2002-12-18 AU AU2002358755A patent/AU2002358755A1/en not_active Abandoned
- 2002-12-18 PT PT02793067T patent/PT1456224E/pt unknown
- 2002-12-18 WO PCT/EP2002/014487 patent/WO2003053992A2/en not_active Ceased
- 2002-12-18 DK DK02793067T patent/DK1456224T3/da active
- 2002-12-18 DE DE60209149T patent/DE60209149T2/de not_active Expired - Lifetime
- 2002-12-18 JP JP2003554708A patent/JP4347696B2/ja not_active Expired - Fee Related
- 2002-12-23 US US10/326,262 patent/US7067683B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002358755A1 (en) | 2003-07-09 |
| PT1456224E (pt) | 2006-06-30 |
| EP1456224A2 (en) | 2004-09-15 |
| US20030171346A1 (en) | 2003-09-11 |
| US7067683B2 (en) | 2006-06-27 |
| ES2256576T3 (es) | 2006-07-16 |
| JP4347696B2 (ja) | 2009-10-21 |
| DK1456224T3 (da) | 2006-06-12 |
| JP2005519047A (ja) | 2005-06-30 |
| EP1456224B1 (en) | 2006-02-08 |
| WO2003053992A2 (en) | 2003-07-03 |
| DE60209149D1 (de) | 2006-04-20 |
| ATE317369T1 (de) | 2006-02-15 |
| WO2003053992A3 (en) | 2004-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: BAYER SCHERING PHARMA AG, 13353 BERLIN, DE |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: BAYER SCHERING PHARMA AKIENGESELLSCHAFT, 13353, DE |