NO313876B1 - FremgangsmÕte for fremstilling av 3-(7-amidino-2-naftyl)-2- fenylpropionsyre-derivater og mellomprodukter i denne - Google Patents
FremgangsmÕte for fremstilling av 3-(7-amidino-2-naftyl)-2- fenylpropionsyre-derivater og mellomprodukter i denne Download PDFInfo
- Publication number
- NO313876B1 NO313876B1 NO19995841A NO995841A NO313876B1 NO 313876 B1 NO313876 B1 NO 313876B1 NO 19995841 A NO19995841 A NO 19995841A NO 995841 A NO995841 A NO 995841A NO 313876 B1 NO313876 B1 NO 313876B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- salt
- formula
- group
- naphthyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- 239000000543 intermediate Substances 0.000 title abstract description 6
- NQLOPLZVMKMJJT-UHFFFAOYSA-N 3-(7-carbamimidoylnaphthalen-2-yl)-2-phenylpropanoic acid Chemical class C=1C2=CC(C(=N)N)=CC=C2C=CC=1CC(C(O)=O)C1=CC=CC=C1 NQLOPLZVMKMJJT-UHFFFAOYSA-N 0.000 title 1
- -1 aromatic amidine Chemical class 0.000 claims abstract description 156
- 150000003839 salts Chemical class 0.000 claims abstract description 87
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- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 22
- 125000002252 acyl group Chemical group 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
- 230000014508 negative regulation of coagulation Effects 0.000 abstract description 2
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
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- 238000009835 boiling Methods 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
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- 238000005984 hydrogenation reaction Methods 0.000 description 4
- VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 description 4
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 4
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
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- YLYAGXMAOLWCSE-WLKYSPGFSA-N Cl.Cl.C1=CC([C@H](CC=2C=C3C=C(C=CC3=CC=2)C(N)=N)C(=O)OCC)=CC=C1O[C@H]1CCNC1 Chemical compound Cl.Cl.C1=CC([C@H](CC=2C=C3C=C(C=CC3=CC=2)C(N)=N)C(=O)OCC)=CC=C1O[C@H]1CCNC1 YLYAGXMAOLWCSE-WLKYSPGFSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 238000006345 epimerization reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000002443 hydroxylamines Chemical class 0.000 description 3
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- MVNXETBTTGVOLO-WLKYSPGFSA-N (2s)-3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-[(3s)-1-ethanimidoylpyrrolidin-3-yl]oxyphenyl]propanoic acid;dihydrochloride Chemical compound Cl.Cl.C1N(C(=N)C)CC[C@@H]1OC1=CC=C([C@H](CC=2C=C3C=C(C=CC3=CC=2)C(N)=N)C(O)=O)C=C1 MVNXETBTTGVOLO-WLKYSPGFSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
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- 150000003892 tartrate salts Chemical class 0.000 description 2
- NMJRXFTUIGIPII-NSOVKSMOSA-N tert-butyl (3s)-3-[4-[(2s)-3-(7-cyanonaphthalen-2-yl)-1-ethoxy-1-oxopropan-2-yl]phenoxy]pyrrolidine-1-carboxylate Chemical compound C1=CC([C@H](CC=2C=C3C=C(C=CC3=CC=2)C#N)C(=O)OCC)=CC=C1O[C@H]1CCN(C(=O)OC(C)(C)C)C1 NMJRXFTUIGIPII-NSOVKSMOSA-N 0.000 description 2
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- AGRCGQSFFMCBRE-UXMRNZNESA-N 3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-[(3s)-1-ethanimidoylpyrrolidin-3-yl]oxyphenyl]propanoic acid Chemical compound C1N(C(=N)C)CC[C@@H]1OC1=CC=C(C(CC=2C=C3C=C(C=CC3=CC=2)C(N)=N)C(O)=O)C=C1 AGRCGQSFFMCBRE-UXMRNZNESA-N 0.000 description 1
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- FXSZGKYGUFCBQY-UHFFFAOYSA-N propanoic acid;dihydrochloride Chemical compound Cl.Cl.CCC(O)=O FXSZGKYGUFCBQY-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14204297 | 1997-05-30 | ||
| PCT/JP1998/002379 WO1998054132A1 (fr) | 1997-05-30 | 1998-05-29 | Procede de preparation de derives d'acide 3-(7-amidino-2-naphthyl)-2-phenylpropionique |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO995841D0 NO995841D0 (no) | 1999-11-29 |
| NO995841L NO995841L (no) | 2000-01-20 |
| NO313876B1 true NO313876B1 (no) | 2002-12-16 |
Family
ID=15306044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19995841A NO313876B1 (no) | 1997-05-30 | 1999-11-29 | FremgangsmÕte for fremstilling av 3-(7-amidino-2-naftyl)-2- fenylpropionsyre-derivater og mellomprodukter i denne |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6342609B2 (de) |
| EP (1) | EP0990646B1 (de) |
| JP (1) | JP3241741B2 (de) |
| KR (1) | KR100527833B1 (de) |
| CN (1) | CN1181053C (de) |
| AU (1) | AU7454998A (de) |
| CA (1) | CA2291665A1 (de) |
| DE (1) | DE69823506T2 (de) |
| ES (1) | ES2221984T3 (de) |
| HK (1) | HK1027109A1 (de) |
| NO (1) | NO313876B1 (de) |
| PT (1) | PT990646E (de) |
| TW (1) | TW513402B (de) |
| WO (1) | WO1998054132A1 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6949567B2 (en) | 2001-02-26 | 2005-09-27 | 4Sc Ag | Compounds for the treatment of protozoal diseases |
| CH695999A5 (de) | 2002-02-28 | 2006-11-15 | Wilex Ag | Verfahren zur Herstellung von 3- Amidinophenylalanin-Derivaten. |
| CN100513398C (zh) | 2002-12-03 | 2009-07-15 | Axys药物公司 | 作为因子viia抑制剂的2-(2-羟基联苯-3-基)-1h-苯并咪唑-5-甲脒衍生物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA928276B (en) * | 1991-10-31 | 1993-05-06 | Daiichi Seiyaku Co | Aromatic amidine derivates and salts thereof. |
| JP3457694B2 (ja) * | 1993-02-04 | 2003-10-20 | 第一製薬株式会社 | インフルエンザ感染予防・治療薬 |
| DE4424713A1 (de) * | 1994-07-13 | 1996-01-18 | Boehringer Ingelheim Kg | Substituierte Benzamidine, ihre Herstellung und Verwendung als Arnzneistoffe |
-
1998
- 1998-05-28 TW TW087108341A patent/TW513402B/zh active
- 1998-05-29 KR KR10-1999-7010742A patent/KR100527833B1/ko not_active IP Right Cessation
- 1998-05-29 CN CNB988056216A patent/CN1181053C/zh not_active Expired - Fee Related
- 1998-05-29 ES ES98921879T patent/ES2221984T3/es not_active Expired - Lifetime
- 1998-05-29 CA CA002291665A patent/CA2291665A1/en not_active Abandoned
- 1998-05-29 WO PCT/JP1998/002379 patent/WO1998054132A1/ja active IP Right Grant
- 1998-05-29 PT PT98921879T patent/PT990646E/pt unknown
- 1998-05-29 US US09/424,227 patent/US6342609B2/en not_active Expired - Fee Related
- 1998-05-29 DE DE69823506T patent/DE69823506T2/de not_active Expired - Fee Related
- 1998-05-29 EP EP98921879A patent/EP0990646B1/de not_active Expired - Lifetime
- 1998-05-29 JP JP50049199A patent/JP3241741B2/ja not_active Expired - Fee Related
- 1998-05-29 AU AU74549/98A patent/AU7454998A/en not_active Abandoned
-
1999
- 1999-11-29 NO NO19995841A patent/NO313876B1/no not_active Application Discontinuation
-
2000
- 2000-10-10 HK HK00106396A patent/HK1027109A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0990646B1 (de) | 2004-04-28 |
| NO995841D0 (no) | 1999-11-29 |
| NO995841L (no) | 2000-01-20 |
| WO1998054132A1 (fr) | 1998-12-03 |
| ES2221984T3 (es) | 2005-01-16 |
| TW513402B (en) | 2002-12-11 |
| CN1181053C (zh) | 2004-12-22 |
| JP3241741B2 (ja) | 2001-12-25 |
| DE69823506D1 (de) | 2004-06-03 |
| US20010001802A1 (en) | 2001-05-24 |
| CN1258275A (zh) | 2000-06-28 |
| US6342609B2 (en) | 2002-01-29 |
| DE69823506T2 (de) | 2004-09-23 |
| EP0990646A4 (de) | 2001-01-17 |
| CA2291665A1 (en) | 1998-12-03 |
| PT990646E (pt) | 2004-09-30 |
| KR20010012780A (ko) | 2001-02-26 |
| KR100527833B1 (ko) | 2005-11-09 |
| EP0990646A1 (de) | 2000-04-05 |
| AU7454998A (en) | 1998-12-30 |
| HK1027109A1 (en) | 2001-01-05 |
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| FC2A | Withdrawal, rejection or dismissal of laid open patent application |