PL116421B1 - Process for preparing novel analogs of prostaglandins - Google Patents
Process for preparing novel analogs of prostaglandins Download PDFInfo
- Publication number
- PL116421B1 PL116421B1 PL1976194803A PL19480376A PL116421B1 PL 116421 B1 PL116421 B1 PL 116421B1 PL 1976194803 A PL1976194803 A PL 1976194803A PL 19480376 A PL19480376 A PL 19480376A PL 116421 B1 PL116421 B1 PL 116421B1
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- radical
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Links
- 150000003180 prostaglandins Chemical class 0.000 title claims description 4
- 229940094443 oxytocics prostaglandins Drugs 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- -1 alkyl radical Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 8
- 150000003254 radicals Chemical class 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 229960002986 dinoprostone Drugs 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- SAKGBZWJAIABSY-SAMSIYEGSA-N prostaglandin F3alpha Chemical compound CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O SAKGBZWJAIABSY-SAMSIYEGSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- 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
-
- 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
-
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- 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
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
- C07F9/4059—Compounds containing the structure (RY)2P(=X)-(CH2)n-C(=O)-(CH2)m-Ar, (X, Y = O, S, Se; n>=1, m>=0)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarza¬ nia nowych analogów prostaglandyn, rózniacych sie od odpowiednich znanych prostaglandyn obecnoscia w polozeniu C-<2 grupy aminometylowej luib pod¬ stawionej aminometylowej, w miejsce grupy karbo- kisylowej.Znane prostaglandyny sa pochodnymi kwasu 6- -«[4ttH(2j!Wtetylo) cytalopentylojhekisanokarboksylowe- go-1 o wzorze 1. Sa to zwiazki z serii PGE — pro- stagilamdyna Et (PGEi o wzónze i2), prosltaglandyna Ea (PGE2 o wzorze 3), prosltaglandyna E3 (PGE8 o wzorze 4) i dwuwodoroprostaglandyna Ei (dihy- dro—PGEi o wzorze 5), zwiazki z serii PGFa ¦¦— prostaglaindyna F1(a (PGFiia o wzorze 6), prostaglan. dyna F^a (PGF»a o wzorze 7), prostaglandyna F3a (PGFjia o wzorze 8) i dwuwodoroprostaglandy- na Fi PGFfJ — prostaglandyna F^ iCPGFiP o iwizorze liO), prostaglandyna F^J PL PL
Claims (1)
1. Zastrzezenie patentowe Sposób wytwarzania nowych analogów prosta- gilandyn o wzorze 18, w którym Rt oznacza grupe wodorotlenowa, L4 oznaciza uiklad rodników o wzo¬ rach 19 luib 20 luto mieszanine tych ukladów, w któ¬ rych R3 i R4 oznaczaja atom wodoru, Mi oznacza uklad o wzorze 21 lub 22, w którym R5 oznacza atom wodoru luib rodnik metylowy, R7 oznacza rod¬ nik alkilowy o 1—5 atomach wegla, korzystnie n- -ibutylowy, Yi oznacza rodnik o wzorze trams^-CH— -^CH—, a Zj oznacza rodnik o wzorze cis—CH = = OH— (GHth luib -hCCH^ • oraz farmakologicznie dopuszczalnych addycyjnych soli tych zwiazków z kwasami, znamienny tym, ze prostaglandyne ty¬ pu amiklu o wzorze 23, w którym Li, Ylt Mj R8, R7 i Zi maja wyzej podane znaczenie podidaje sie reakcji z wodorkiem MowogMnowym i wytworzo¬ ny produkt ewentualnie przeprowadza sie w far¬ makologicznie dopuszczalna sól addycyjna na dro¬ dze reakcji z farmakologicznie dopuszczalnym kwa¬ sem.116421 COOH WZÓR 1 COOH WZÓR 2 COOH COOH O WZÓR l* .'\^-^^COOH H^ "OH WZÓR 5 COOH WZÓR 3 _^/-COOH ^ZÓR 6 COOH WZÓR 8 COOH WZÓR 9116421 COOH HÓ H' ^OH WZÓR 11 COOH hT "OH WZÓR 13 COOH COOH HO H ^OH WZÓR 12 COOH COOH HT "OH ^ R R3 *U R3 RA WZÓR 16 WZÓR 19 WZÓR 20 R5 OH WZÓR 21116421 HO, O II CH^Z^C- NH2 WZÓR 22 , 'Y-C-C-FL R 1 II II 7 8 M1 L1 WZÓR 23 HO Re CH^- CH2NH2 Yl ~ C C ~ R ry I II II / M, Li WZÓR 18 SCHEMAT 1 HO RC CH2-Z - COOH Y.-C—C-Rn 1 II II 1 WZÓR 25 O O HO CH2-ZfC-0-C-R1 ,- -YrC-C-R7 R8 1 II II ' M1 L1 O WZÓR 2h H0 CH-Z-C-NH2 V\y,-c-c-r7 R " '! 8 M, L, R WZÓR 23 SCHEMAT 2 PL PL PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64527675A | 1975-12-29 | 1975-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL116421B1 true PL116421B1 (en) | 1981-06-30 |
Family
ID=24588384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976194803A PL116421B1 (en) | 1975-12-29 | 1976-12-29 | Process for preparing novel analogs of prostaglandins |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US4085139A (pl) |
| JP (1) | JPS5283351A (pl) |
| AU (1) | AU502349B2 (pl) |
| BE (1) | BE849963A (pl) |
| CA (1) | CA1077473A (pl) |
| CH (1) | CH629747A5 (pl) |
| DE (1) | DE2658207A1 (pl) |
| ES (1) | ES454181A1 (pl) |
| FR (1) | FR2336924A1 (pl) |
| GB (2) | GB1554041A (pl) |
| HU (1) | HU178365B (pl) |
| IL (1) | IL50997A (pl) |
| MX (1) | MX4940E (pl) |
| NL (1) | NL7614389A (pl) |
| PL (1) | PL116421B1 (pl) |
| SE (1) | SE7614584L (pl) |
| SU (1) | SU731895A3 (pl) |
| ZA (1) | ZA767416B (pl) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4048058A (en) * | 1975-08-13 | 1977-09-13 | Standard Oil Company (Indiana) | Methods to be used in reforming processes employing multi-metallic catalysts |
| US4267315A (en) * | 1979-05-01 | 1981-05-12 | The Upjohn Company | 2-Decarboxy-2-aminomethyl-11a-methano-TXA2 compounds |
| US4292445A (en) * | 1980-04-28 | 1981-09-29 | The Upjohn Company | Amide and sulfonamide derivatives of 2-decarboxy-2-aminomethyl-PG-type compounds |
| CA1241324A (en) | 1984-03-08 | 1988-08-30 | Paul A. Aristoff | Interphenylene carbacyclin derivatives |
| US5270049A (en) * | 1990-11-09 | 1993-12-14 | Allergan, Inc. | 2-decarboxyl-2-aminoalkyl-prostaglandins as ocular hypotensives |
| HU223068B1 (hu) * | 1995-12-20 | 2004-03-01 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | Eljárás PGE1 prosztanoid előállítására |
| WO2010102078A1 (en) | 2009-03-04 | 2010-09-10 | Allergan, Inc. | Enhanced bimatoprost ophthalmic solution |
| US7851504B2 (en) | 2005-03-16 | 2010-12-14 | Allergan, Inc. | Enhanced bimatoprost ophthalmic solution |
| WO2011008756A1 (en) | 2009-07-13 | 2011-01-20 | Irix Pharmaceuticals | Synthesis of prostanoids |
| US9522153B2 (en) | 2009-12-22 | 2016-12-20 | Allergan, Inc. | Compositions and methods for lowering intraocular pressure |
| HUP1000284A3 (en) * | 2010-06-01 | 2012-08-28 | Avidin Kft | Use of derivatives of pgf1-alpha for preparation of medicament for reducing inflammation |
| WO2015048736A1 (en) | 2013-09-30 | 2015-04-02 | Irix Pharmaceuticals, Inc. | Novel synthesis routes for prostaglandins and prostaglandin intermediates using metathesis |
| CN104860860B (zh) * | 2015-04-29 | 2017-09-19 | 东北制药集团股份有限公司 | 一种卡前列酯的纯化制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2166971A (en) * | 1932-09-14 | 1939-07-25 | Ig Farbenindustrie Ag | Production of amines |
| GB971700A (en) * | 1961-02-02 | 1964-09-30 | Boots Pure Drug Co Ltd | Anti-Inflammatory Agents |
| US3647804A (en) * | 1970-02-27 | 1972-03-07 | Upjohn Co | Cycloalkanecarboxamides |
| US3852296A (en) * | 1971-07-16 | 1974-12-03 | Richardson Merrell Spa | Mannich bases of cyclopentanones and cyclopent-2-enones and process of preparing the same |
| US3987087A (en) * | 1971-07-29 | 1976-10-19 | The Upjohn Company | Phenyl-substituted prostaglandin-f type analogs |
| US3954741A (en) * | 1972-06-07 | 1976-05-04 | Pfizer Inc. | N-substituted prostaglandin carboxamides |
| US3987085A (en) * | 1972-09-15 | 1976-10-19 | The Upjohn Company | 8β,11β,12α-PGF2.sub.α compounds |
-
1976
- 1976-08-30 US US05/719,053 patent/US4085139A/en not_active Expired - Lifetime
- 1976-08-30 US US05/719,054 patent/US4081478A/en not_active Expired - Lifetime
- 1976-08-30 US US05/719,055 patent/US4073808A/en not_active Expired - Lifetime
- 1976-08-30 US US05/719,056 patent/US4122282A/en not_active Expired - Lifetime
- 1976-11-16 CA CA265,797A patent/CA1077473A/en not_active Expired
- 1976-11-25 IL IL50997A patent/IL50997A/xx unknown
- 1976-12-09 AU AU20396/76A patent/AU502349B2/en not_active Expired
- 1976-12-13 ES ES454181A patent/ES454181A1/es not_active Expired
- 1976-12-13 ZA ZA767416A patent/ZA767416B/xx unknown
- 1976-12-15 CH CH1579476A patent/CH629747A5/de not_active IP Right Cessation
- 1976-12-21 HU HU76UO132A patent/HU178365B/hu unknown
- 1976-12-22 DE DE19762658207 patent/DE2658207A1/de not_active Withdrawn
- 1976-12-23 JP JP15439276A patent/JPS5283351A/ja active Granted
- 1976-12-23 GB GB53739/76A patent/GB1554041A/en not_active Expired
- 1976-12-23 GB GB30065/78A patent/GB1554042A/en not_active Expired
- 1976-12-24 NL NL7614389A patent/NL7614389A/xx not_active Application Discontinuation
- 1976-12-27 SE SE7614584A patent/SE7614584L/xx not_active Application Discontinuation
- 1976-12-28 FR FR7639303A patent/FR2336924A1/fr active Granted
- 1976-12-28 SU SU762434653A patent/SU731895A3/ru active
- 1976-12-29 BE BE173722A patent/BE849963A/xx not_active IP Right Cessation
- 1976-12-29 PL PL1976194803A patent/PL116421B1/pl unknown
-
1977
- 1977-01-03 MX MX775256U patent/MX4940E/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4073808A (en) | 1978-02-14 |
| FR2336924A1 (fr) | 1977-07-29 |
| IL50997A (en) | 1982-05-31 |
| AU502349B2 (en) | 1979-07-19 |
| IL50997A0 (en) | 1977-01-31 |
| FR2336924B1 (pl) | 1984-08-17 |
| GB1554041A (en) | 1979-10-17 |
| SE7614584L (sv) | 1977-06-30 |
| ZA767416B (en) | 1977-11-30 |
| BE849963A (fr) | 1977-06-29 |
| US4122282A (en) | 1978-10-24 |
| US4081478A (en) | 1978-03-28 |
| SU731895A3 (ru) | 1980-04-30 |
| JPS5283351A (en) | 1977-07-12 |
| MX4940E (es) | 1983-01-10 |
| JPS5744666B2 (pl) | 1982-09-22 |
| US4085139A (en) | 1978-04-18 |
| NL7614389A (nl) | 1977-07-01 |
| GB1554042A (en) | 1979-10-17 |
| ES454181A1 (es) | 1977-12-16 |
| HU178365B (en) | 1982-04-28 |
| AU2039676A (en) | 1978-06-15 |
| CH629747A5 (de) | 1982-05-14 |
| DE2658207A1 (de) | 1977-07-07 |
| CA1077473A (en) | 1980-05-13 |
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