FI110001B - 6-substituerade 5-oxo-oktahydrotiazolo[3,2-a]azepin-3-karboxylsyraderivat och förfarande för framställning av de samma samt deras användning - Google Patents
6-substituerade 5-oxo-oktahydrotiazolo[3,2-a]azepin-3-karboxylsyraderivat och förfarande för framställning av de samma samt deras användning Download PDFInfo
- Publication number
- FI110001B FI110001B FI961199A FI961199A FI110001B FI 110001 B FI110001 B FI 110001B FI 961199 A FI961199 A FI 961199A FI 961199 A FI961199 A FI 961199A FI 110001 B FI110001 B FI 110001B
- Authority
- FI
- Finland
- Prior art keywords
- derivative
- oxo
- azepine
- pharmacologically acceptable
- acceptable salt
- Prior art date
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- FVZLXIARAAOVCZ-UHFFFAOYSA-N 1h-azepine-3-carboxylic acid Chemical class OC(=O)C1=CNC=CC=C1 FVZLXIARAAOVCZ-UHFFFAOYSA-N 0.000 title claims description 42
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- -1 6-substituted 5-oxo-octahydrothiazolo [3,2-a] azepine-3-carboxylic acid Chemical class 0.000 claims description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
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- JKJPBCBNQWFKSO-UHFFFAOYSA-N 5-oxo-3,6,7,8,9,9a-hexahydro-2h-[1,3]thiazolo[3,2-a]azepine-3-carboxylic acid Chemical class C1CCCC(=O)N2C(C(=O)O)CSC21 JKJPBCBNQWFKSO-UHFFFAOYSA-N 0.000 claims 1
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- 201000006370 kidney failure Diseases 0.000 description 1
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 208000012866 low blood pressure Diseases 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
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- VLBGLJUJUMYKPM-ILUDGRTOSA-N methyl (4R)-2-[(1R,2R)-2-[(2S)-2-acetamido-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]cyclohexyl]-1,3-thiazolidine-4-carboxylate Chemical compound C(C)(=O)N[C@@H](C[C@@H]1[C@@H](CCCC1)C1SC[C@H](N1)C(=O)OC)C(=O)OC(C)(C)C VLBGLJUJUMYKPM-ILUDGRTOSA-N 0.000 description 1
- KWPZBHSRCDQNAJ-UHFFFAOYSA-N methyl 5-oxo-3,6,7,8,9,9a-hexahydro-2H-[1,3]thiazolo[3,2-a]azepine-3-carboxylate Chemical compound COC(=O)C1CSC2N1C(CCCC2)=O KWPZBHSRCDQNAJ-UHFFFAOYSA-N 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 210000000110 microvilli Anatomy 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000692 natriuretic peptide Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000036515 potency Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- BTTJPVWNQIUSOX-RYUDHWBXSA-N tert-butyl (2s,5s)-1-acetyl-5-ethylpiperidine-2-carboxylate Chemical compound CC[C@H]1CC[C@@H](C(=O)OC(C)(C)C)N(C(C)=O)C1 BTTJPVWNQIUSOX-RYUDHWBXSA-N 0.000 description 1
- OHUYVKOABGNKDQ-ONGXEEELSA-N tert-butyl (2s,5s)-1-acetyl-5-methylpiperidine-2-carboxylate Chemical compound C[C@H]1CC[C@@H](C(=O)OC(C)(C)C)N(C(C)=O)C1 OHUYVKOABGNKDQ-ONGXEEELSA-N 0.000 description 1
- JGAGFJYLYRLZJD-RDBSUJKOSA-N tert-butyl (3s,4ar,8ar)-2-acetyl-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinoline-3-carboxylate Chemical compound C1CCC[C@@H]2C[C@@H](C(=O)OC(C)(C)C)N(C(=O)C)C[C@@H]21 JGAGFJYLYRLZJD-RDBSUJKOSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WGHUNMFFLAMBJD-UHFFFAOYSA-M tetraethylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CC[N+](CC)(CC)CC WGHUNMFFLAMBJD-UHFFFAOYSA-M 0.000 description 1
- ZCWKIFAQRXNZCH-UHFFFAOYSA-M tetramethylazanium;perchlorate Chemical compound C[N+](C)(C)C.[O-]Cl(=O)(=O)=O ZCWKIFAQRXNZCH-UHFFFAOYSA-M 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 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
- 238000013519 translation Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16548194 | 1994-07-18 | ||
| JP6165481A JPH0827156A (ja) | 1994-07-18 | 1994-07-18 | アミノ酸誘導体の製造方法 |
| JP19918094A JP3444666B2 (ja) | 1994-08-24 | 1994-08-24 | （２ｓ， ３ｓ）−３− メチル−２− チオペンタン酸誘導体の製造方法 |
| JP19918094 | 1994-08-24 | ||
| JP6306468A JPH08165293A (ja) | 1994-12-09 | 1994-12-09 | 置換チアゾロ［３，２−ａ］アゼピン誘導体 |
| JP30646894 | 1994-12-09 | ||
| JP9501139 | 1995-06-07 | ||
| PCT/JP1995/001139 WO1996002549A1 (fr) | 1994-07-18 | 1995-06-07 | DERIVE DE THIAZOLO[3,2-α]AZEPINE A SUBSTITUTION |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI961199A0 FI961199A0 (sv) | 1996-03-14 |
| FI961199A FI961199A (sv) | 1996-05-13 |
| FI110001B true FI110001B (sv) | 2002-11-15 |
Family
ID=27322514
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI961199A FI110001B (sv) | 1994-07-18 | 1996-03-14 | 6-substituerade 5-oxo-oktahydrotiazolo[3,2-a]azepin-3-karboxylsyraderivat och förfarande för framställning av de samma samt deras användning |
| FI20011154A FI113656B (sv) | 1994-07-18 | 2001-06-01 | 6-amino-5-oxo-oktahydrotiazolo[3,2-a]azepin-3-karboxylsyraderivat användabara som mellanprodukt |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI20011154A FI113656B (sv) | 1994-07-18 | 2001-06-01 | 6-amino-5-oxo-oktahydrotiazolo[3,2-a]azepin-3-karboxylsyraderivat användabara som mellanprodukt |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US5789403A (sv) |
| EP (1) | EP0719779B1 (sv) |
| KR (1) | KR100284247B1 (sv) |
| CN (2) | CN1053908C (sv) |
| AT (1) | ATE254622T1 (sv) |
| AU (1) | AU694233B2 (sv) |
| CA (1) | CA2171334C (sv) |
| DE (1) | DE69532155T2 (sv) |
| DK (1) | DK0719779T3 (sv) |
| ES (1) | ES2210292T3 (sv) |
| FI (2) | FI110001B (sv) |
| HU (1) | HU225916B1 (sv) |
| MX (1) | MX9601017A (sv) |
| NO (1) | NO308077B1 (sv) |
| NZ (1) | NZ287557A (sv) |
| PT (1) | PT719779E (sv) |
| WO (1) | WO1996002549A1 (sv) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5650408A (en) * | 1995-06-07 | 1997-07-22 | Karanewsky; Donald S. | Thiazolo benzazepine containing dual action inhibitors |
| WO1998034636A1 (fr) * | 1997-02-05 | 1998-08-13 | Suntory Limited | Compositions medicinales pour traiter les cardiopathies induites par l'hypertrophie cardiaque |
| US9823092B2 (en) | 2014-10-31 | 2017-11-21 | Allegro Microsystems, Llc | Magnetic field sensor providing a movement detector |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA821904B (en) * | 1981-03-23 | 1983-01-26 | Merck & Co Inc | Bicyclic lactams as anthihypertensives |
| US4415496A (en) * | 1981-03-23 | 1983-11-15 | Merck & Co., Inc. | Bicyclic lactams |
| US4617301A (en) * | 1983-06-22 | 1986-10-14 | Merck & Co., Inc. | Sulfoxide and sulfone derivatives of bicyclic lactams as antihypertensives |
| JPS6056790A (ja) * | 1983-09-03 | 1985-04-02 | 山陽科学株式会社 | 荷役用マット |
| RU2124503C1 (ru) * | 1992-05-18 | 1999-01-10 | И.Р.Сквибб энд Санз, Инк. | Гетероциклические азотсодержащие производные карбоновой кислоты, способ их получения и фармацевтическая композиция |
| DE69329701T2 (de) * | 1992-10-30 | 2001-05-10 | Merrell Pharma Inc | Mercaptoacetylamid substituiertes bizyclisches laktam zur verwendung als enkephalinase und ace-hemmer |
| US5650408A (en) * | 1995-06-07 | 1997-07-22 | Karanewsky; Donald S. | Thiazolo benzazepine containing dual action inhibitors |
-
1995
- 1995-06-07 DE DE69532155T patent/DE69532155T2/de not_active Expired - Fee Related
- 1995-06-07 PT PT95921127T patent/PT719779E/pt unknown
- 1995-06-07 US US08/612,864 patent/US5789403A/en not_active Expired - Lifetime
- 1995-06-07 ES ES95921127T patent/ES2210292T3/es not_active Expired - Lifetime
- 1995-06-07 CN CN95190779A patent/CN1053908C/zh not_active Expired - Fee Related
- 1995-06-07 KR KR1019960701358A patent/KR100284247B1/ko not_active IP Right Cessation
- 1995-06-07 NZ NZ287557A patent/NZ287557A/en not_active IP Right Cessation
- 1995-06-07 AU AU26301/95A patent/AU694233B2/en not_active Ceased
- 1995-06-07 HU HU9600679A patent/HU225916B1/hu not_active IP Right Cessation
- 1995-06-07 AT AT95921127T patent/ATE254622T1/de not_active IP Right Cessation
- 1995-06-07 MX MX9601017A patent/MX9601017A/es not_active IP Right Cessation
- 1995-06-07 EP EP95921127A patent/EP0719779B1/en not_active Expired - Lifetime
- 1995-06-07 WO PCT/JP1995/001139 patent/WO1996002549A1/ja active IP Right Grant
- 1995-06-07 CA CA002171334A patent/CA2171334C/en not_active Expired - Fee Related
- 1995-06-07 DK DK95921127T patent/DK0719779T3/da active
-
1996
- 1996-03-14 NO NO19961051A patent/NO308077B1/no not_active IP Right Cessation
- 1996-03-14 FI FI961199A patent/FI110001B/sv active
-
1998
- 1998-05-27 US US09/085,729 patent/US6051705A/en not_active Expired - Fee Related
-
1999
- 1999-10-28 CN CNB991236092A patent/CN1170832C/zh not_active Expired - Fee Related
-
2001
- 2001-06-01 FI FI20011154A patent/FI113656B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE254622T1 (de) | 2003-12-15 |
| NO961051D0 (no) | 1996-03-14 |
| DE69532155D1 (de) | 2003-12-24 |
| FI20011154A (sv) | 2001-06-01 |
| KR100284247B1 (ko) | 2001-10-24 |
| CN1262275A (zh) | 2000-08-09 |
| WO1996002549A1 (fr) | 1996-02-01 |
| FI961199A (sv) | 1996-05-13 |
| US6051705A (en) | 2000-04-18 |
| AU2630195A (en) | 1996-02-16 |
| AU694233B2 (en) | 1998-07-16 |
| PT719779E (pt) | 2004-04-30 |
| CN1134152A (zh) | 1996-10-23 |
| HU225916B1 (en) | 2007-12-28 |
| CA2171334C (en) | 2008-10-21 |
| EP0719779A4 (en) | 1996-12-18 |
| ES2210292T3 (es) | 2004-07-01 |
| HU9600679D0 (en) | 1996-05-28 |
| DE69532155T2 (de) | 2004-08-19 |
| MX9601017A (es) | 1997-10-31 |
| CN1170832C (zh) | 2004-10-13 |
| HUT76477A (en) | 1997-09-29 |
| DK0719779T3 (da) | 2004-03-22 |
| US5789403A (en) | 1998-08-04 |
| EP0719779B1 (en) | 2003-11-19 |
| EP0719779A1 (en) | 1996-07-03 |
| FI113656B (sv) | 2004-05-31 |
| KR960704898A (ko) | 1996-10-09 |
| NZ287557A (en) | 1997-04-24 |
| NO308077B1 (no) | 2000-07-17 |
| FI961199A0 (sv) | 1996-03-14 |
| NO961051L (no) | 1996-05-10 |
| CA2171334A1 (en) | 1996-02-01 |
| CN1053908C (zh) | 2000-06-28 |
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| Date | Code | Title | Description |
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| PC | Transfer of assignment of patent |
Owner name: EISAI R&D MANAGEMENT CO., LTD. Free format text: EISAI R&D MANAGEMENT CO., LTD. |