SE8504616D0 - carbacyclin analogues - Google Patents
carbacyclin analoguesInfo
- Publication number
- SE8504616D0 SE8504616D0 SE8504616A SE8504616A SE8504616D0 SE 8504616 D0 SE8504616 D0 SE 8504616D0 SE 8504616 A SE8504616 A SE 8504616A SE 8504616 A SE8504616 A SE 8504616A SE 8504616 D0 SE8504616 D0 SE 8504616D0
- Authority
- SE
- Sweden
- Prior art keywords
- alkyl
- substd
- opt
- beta
- alpha
- Prior art date
Links
- XZFRIPGNUQRGPI-WLPVIMDJSA-N Carbacyclin Chemical class C1\C(=C\CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 XZFRIPGNUQRGPI-WLPVIMDJSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 5
- -1 pyrrolidino, piperidino, morpholino, piperazino Chemical group 0.000 abstract 5
- 125000001153 fluoro group Chemical group F* 0.000 abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 101100328892 Arabidopsis thaliana COL4 gene Proteins 0.000 abstract 1
- 101100237842 Xenopus laevis mmp18 gene Proteins 0.000 abstract 1
- 230000009858 acid secretion Effects 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 239000003699 antiulcer agent Substances 0.000 abstract 1
- 125000005605 benzo group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000001768 cations Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000004344 phenylpropyl group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 230000003637 steroidlike Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/005—Analogues or derivatives having the five membered ring replaced by other rings
- C07C405/0075—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system
- C07C405/0083—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system which is only ortho or peri condensed, e.g. carbacyclins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Abstract
(A) Carbacycline derivs. of formulae (X) and (X1) are new. n is 1 or 2. L1 is alpha-R3, beta-R4; beta-R3 or a mixt. of both; R3 and R4 being each H, methyl or fluoro, M1 is alpha-hydroxy, beta-R5 or alpha-R5, beta-hydroxy; R5 being H or methyl. R7 is CmH2m. CH3 (m is 1-5); phenoxy opt. substd. by 1-3 of chloro, fluoro, trifluoromethyl, 1-3C alkyl or alkoxy phenyl, benzyl, phenethyl or phenylpropyl, all opt. ring-substd. as phenoxy; cis-CH=CH.CH2.CH3; (CH2)2. CH(OH).CH3 or (CH2)3.CH=C(CH3)2. R8 is H, hydroxymethyl or hydroxy. R15 is H or fluoro R16 is hydrogen or together with R17 is methylene. R17 is H or 1-4C alkyl. R20, R21, R22, R23 or R4 can all be H (2 R22 alpha or beta); or R20 is H, R21 and R33 form a second C-C bond, and R23 and R24 form a second bond or are both H; or R22, R23 and R24 are all H (R22 alpha or beta) and R21 and R20 are together oxo, or R20 is H and R21 alpha or beta hydroxy. X1 is COOR1, hydroxymethyl, COL4, or CH2NL2L3 or R1 is a cation. L4 is NR51R52; pyrrolidino, piperidino, morpholino, piperazino, hexamethyl eneimino, pyrrolino or 3,4-didehhydropiperidinyl (opt. substd). N(R53).COR51 or N(R53).SO2.R51 R51 and R52 are H, 1-12C alkyl, 3-10C cycloalkyl, 7-12C aralkyl, phenyl (opt. substd. by 1-3 chloro, 1-3C alkyl, hydroxy, carboxy, 2-5C alkoxycarbonyl or nitro), 2-5C (carboxy-, carbamoyl- or cyano) alkyl, 3-6C acetyl alkyl, 7-11C benzo(sic)alkyl (opt.substd) pyridyl (opt. substd). 6-9C pyridylalkyl (opt. substd.) or is 1-4C mono- di- or tri-hydroxyalkyl; at most one of R51 and R52 is H or alkyl. R53 is H or 1-4C alkyl, and is N(R3). COR51, R51 cannot be H. L2 and L3 are H or 1-4C alkyl. Y is cis or trans vinylene, ethylene or CC Z1 is CH2.(CH2)f. C(R2)2; trans-CH2. CH=CH, or -Ph-(CH2)g R2 is H or fluoro f is 0-3, Ph is 1,2-,1,3- or 1,4-phenylene. g is 0-3. (X) and (X1) are useful in human and veterinary medicine as antithromotics, antiulcer agents (reducing acid secretion and counteracting effects of non-steroidal antiinflam
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/125,608 US4338457A (en) | 1980-02-28 | 1980-02-28 | Composition and process |
| US13505580A | 1980-03-28 | 1980-03-28 | |
| US14054680A | 1980-04-15 | 1980-04-15 | |
| US14295380A | 1980-04-23 | 1980-04-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8504616L SE8504616L (en) | 1985-10-04 |
| SE8504616D0 true SE8504616D0 (en) | 1985-10-04 |
Family
ID=27494588
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8100564A SE453594B (en) | 1980-02-28 | 1981-01-28 | carbacyclin analogues |
| SE8504618A SE8504618D0 (en) | 1980-02-28 | 1985-10-04 | carbacyclin analogues |
| SE8504615A SE8504615L (en) | 1980-02-28 | 1985-10-04 | carbacyclin analogues |
| SE8504619A SE8504619L (en) | 1980-02-28 | 1985-10-04 | carbacyclin analogues |
| SE8504616A SE8504616D0 (en) | 1980-02-28 | 1985-10-04 | carbacyclin analogues |
| SE8504617A SE8504617D0 (en) | 1980-02-28 | 1985-10-04 | carbacyclin analogues |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8100564A SE453594B (en) | 1980-02-28 | 1981-01-28 | carbacyclin analogues |
| SE8504618A SE8504618D0 (en) | 1980-02-28 | 1985-10-04 | carbacyclin analogues |
| SE8504615A SE8504615L (en) | 1980-02-28 | 1985-10-04 | carbacyclin analogues |
| SE8504619A SE8504619L (en) | 1980-02-28 | 1985-10-04 | carbacyclin analogues |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8504617A SE8504617D0 (en) | 1980-02-28 | 1985-10-04 | carbacyclin analogues |
Country Status (12)
| Country | Link |
|---|---|
| JP (2) | JPH02167248A (en) |
| AU (2) | AU542861B2 (en) |
| CA (1) | CA1201712A (en) |
| CH (2) | CH655308A5 (en) |
| DE (4) | DE3153460C2 (en) |
| FR (1) | FR2484413B1 (en) |
| GB (1) | GB2070596B (en) |
| HK (1) | HK6989A (en) |
| IL (1) | IL61936A (en) |
| IT (1) | IT1144901B (en) |
| NL (1) | NL8100959A (en) |
| SE (6) | SE453594B (en) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3237200A1 (en) * | 1982-10-05 | 1984-04-05 | Schering AG, 1000 Berlin und 4709 Bergkamen | 5-FLUORCARBACYCLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
| CA1201712A (en) * | 1980-02-28 | 1986-03-11 | Paul A. Aristoff | Carbacyclin analogs |
| DE3048906A1 (en) * | 1980-12-19 | 1982-07-15 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | NEW CARBACYCLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
| DE3142733A1 (en) * | 1981-10-23 | 1983-05-05 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | METHOD FOR PRODUCING CARBACYCLIN INTERMEDIATE PRODUCTS |
| DE3146278C2 (en) * | 1981-11-21 | 1984-10-31 | Grünenthal GmbH, 5190 Stolberg | cis-bicyclo [3.3.0] octane derivatives, medicaments containing them and processes for the preparation of these compounds |
| IL67332A (en) * | 1981-12-01 | 1985-12-31 | Chinoin Gyogyszer Es Vegyeszet | Inter-m-phenylene-prostacyclin analogues,process for the preparation thereof and pharmaceutical compositions containing them |
| DE3204443A1 (en) * | 1982-02-08 | 1983-08-18 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | NEW CARBACYCLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
| US4487961A (en) * | 1982-02-16 | 1984-12-11 | The Upjohn Company | 9-Substituted carbacyclin analogs |
| US4533749A (en) * | 1982-02-16 | 1985-08-06 | The Upjohn Company | 9-Substituted carbacyclin analogs |
| US4486598A (en) * | 1982-02-22 | 1984-12-04 | The Upjohn Company | Carbacyclin analogs |
| US4490555A (en) * | 1982-03-19 | 1984-12-25 | The Upjohn Company | 9-Substituted carbacyclin analogs |
| US4487960A (en) * | 1982-04-19 | 1984-12-11 | The Upjohn Company | 9-Substituted carbacyclin analogs |
| HU190007B (en) * | 1982-05-06 | 1986-08-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | Process for producing new aromatic prostacylin analogues |
| DE3225287A1 (en) * | 1982-07-02 | 1984-01-05 | Schering AG, 1000 Berlin und 4709 Bergkamen | NEW CARBACYCLINAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
| DE3225288A1 (en) * | 1982-07-02 | 1984-01-19 | Schering AG, 1000 Berlin und 4709 Bergkamen | NEW CARBACYCLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
| DE3408699A1 (en) * | 1984-03-08 | 1985-09-12 | Schering AG, 1000 Berlin und 4709 Bergkamen | NEW CARBACYCLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
| US4683330A (en) * | 1984-03-08 | 1987-07-28 | The Upjohn Company | Interphenylene carbacyclin derivatives |
| US4668814A (en) * | 1984-03-08 | 1987-05-26 | The Upjohn Company | Interphenylene carbacyclin derivatives |
| EP0175450B1 (en) * | 1984-07-18 | 1989-03-22 | The Upjohn Company | An interphenylene-carbacyclin compound |
| DE3428266A1 (en) * | 1984-07-27 | 1986-01-30 | Schering AG, 1000 Berlin und 4709 Bergkamen | NEW CARBACYCLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
| DE19722849A1 (en) * | 1997-05-23 | 1998-11-26 | Schering Ag | Leukotriene B¶4¶ antagonists, especially 3-oxa-tetra-hydronaphthalene LTB¶4¶ antagonists |
| US6700025B2 (en) * | 2001-01-05 | 2004-03-02 | United Therapeutics Corporation | Process for stereoselective synthesis of prostacyclin derivatives |
| CA2526534C (en) | 2003-05-22 | 2011-07-12 | United Therapeutics Corporation | Compounds and methods for delivery of prostacyclin analogs |
| JP5190200B2 (en) * | 2003-12-16 | 2013-04-24 | ユナイテッド セラピューティクス コーポレイション | Use of treprostinil for the treatment and prevention of ischemic lesions |
| US20090124697A1 (en) | 2003-12-16 | 2009-05-14 | United Therapeutics Corporation | Inhalation formulations of treprostinil |
| CA2710725C (en) | 2010-07-22 | 2017-08-01 | Alphora Research Inc. | Protected aldehydes for use as intermediates in chemical syntheses, and processes for their preparation |
| CA2726599C (en) | 2010-12-30 | 2017-07-25 | Alphora Research Inc. | Process for treprostinil salt preparation |
| JP2016517410A (en) | 2013-03-14 | 2016-06-16 | ユナイテッド セラピューティクス コーポレイション | Solid form of treprostinil |
| KR101830693B1 (en) * | 2016-04-28 | 2018-02-21 | 연성정밀화학(주) | Process for Preparing Treprostinil and Intermediate Therefor |
| HU231212B1 (en) | 2018-04-16 | 2021-11-29 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Process for production of iloprost |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5495552A (en) * | 1978-01-06 | 1979-07-28 | Sankyo Co Ltd | Prostacyline derivative and its preparation |
| JPS54119441A (en) * | 1978-03-09 | 1979-09-17 | Sumitomo Chem Co Ltd | Novel bicyclooctane derivative |
| DE2912409A1 (en) * | 1978-03-31 | 1979-10-11 | Ono Pharmaceutical Co | 6,9 METHANO PGI LOW 2 ANALOGS |
| US4180657A (en) * | 1978-08-14 | 1979-12-25 | The Upjohn Company | Acyl-substituted phenyl esters of prostacyclin-type compounds |
| US4192891A (en) * | 1979-04-25 | 1980-03-11 | E. R. Squibb & Sons, Inc. | Prostacyclin analogs and their use in inhibition of arachidonic acid-induced platelet aggregation and bronchoconstriction |
| US4338457A (en) * | 1980-02-28 | 1982-07-06 | The Upjohn Company | Composition and process |
| CA1201712A (en) * | 1980-02-28 | 1986-03-11 | Paul A. Aristoff | Carbacyclin analogs |
| DE3121155A1 (en) * | 1981-05-22 | 1982-12-09 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | NEW CARBACYCLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
-
1981
- 1981-01-16 CA CA000368710A patent/CA1201712A/en not_active Expired
- 1981-01-20 IL IL61936A patent/IL61936A/en unknown
- 1981-01-23 AU AU66606/81A patent/AU542861B2/en not_active Expired
- 1981-01-28 SE SE8100564A patent/SE453594B/en not_active IP Right Cessation
- 1981-01-30 GB GB8102901A patent/GB2070596B/en not_active Expired
- 1981-02-16 DE DE3153460A patent/DE3153460C2/de not_active Expired - Lifetime
- 1981-02-16 DE DE3153390A patent/DE3153390C2/de not_active Expired
- 1981-02-16 DE DE3153474A patent/DE3153474C2/de not_active Expired - Lifetime
- 1981-02-16 DE DE3105588A patent/DE3105588A1/en active Granted
- 1981-02-17 CH CH1786/84A patent/CH655308A5/en not_active IP Right Cessation
- 1981-02-17 CH CH1038/81A patent/CH648017A5/en not_active IP Right Cessation
- 1981-02-26 IT IT20019/81A patent/IT1144901B/en active
- 1981-02-27 NL NL8100959A patent/NL8100959A/en active Search and Examination
- 1981-02-27 FR FR8103965A patent/FR2484413B1/en not_active Expired
-
1985
- 1985-01-30 AU AU38208/85A patent/AU567392B2/en not_active Expired
- 1985-10-04 SE SE8504618A patent/SE8504618D0/en not_active Application Discontinuation
- 1985-10-04 SE SE8504615A patent/SE8504615L/en not_active Application Discontinuation
- 1985-10-04 SE SE8504619A patent/SE8504619L/en not_active Application Discontinuation
- 1985-10-04 SE SE8504616A patent/SE8504616D0/en not_active Application Discontinuation
- 1985-10-04 SE SE8504617A patent/SE8504617D0/en not_active Application Discontinuation
-
1989
- 1989-01-19 HK HK69/89A patent/HK6989A/en not_active IP Right Cessation
- 1989-10-24 JP JP1275132A patent/JPH02167248A/en active Granted
-
1993
- 1993-01-22 JP JP5025993A patent/JPH06145085A/en active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAV | Patent application has lapsed |
Ref document number: 8504616-7 Effective date: 19920621 |