PL107544B1 - Sposob wytwarzania nowych pochodnych prostaglandyn - Google Patents
Sposob wytwarzania nowych pochodnych prostaglandyn Download PDFInfo
- Publication number
- PL107544B1 PL107544B1 PL1977210101A PL21010177A PL107544B1 PL 107544 B1 PL107544 B1 PL 107544B1 PL 1977210101 A PL1977210101 A PL 1977210101A PL 21010177 A PL21010177 A PL 21010177A PL 107544 B1 PL107544 B1 PL 107544B1
- Authority
- PL
- Poland
- Prior art keywords
- pgei
- formula
- compounds
- aza
- deoxy
- Prior art date
Links
- 150000003180 prostaglandins Chemical class 0.000 title claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 229910014033 C-OH Inorganic materials 0.000 claims 1
- 229910014570 C—OH Inorganic materials 0.000 claims 1
- 230000000694 effects Effects 0.000 description 12
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 11
- 230000008602 contraction Effects 0.000 description 10
- 230000009471 action Effects 0.000 description 7
- 230000000144 pharmacologic effect Effects 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 210000000936 intestine Anatomy 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 210000004291 uterus Anatomy 0.000 description 5
- 230000007883 bronchodilation Effects 0.000 description 4
- 230000001939 inductive effect Effects 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 210000000621 bronchi Anatomy 0.000 description 3
- 229940124630 bronchodilator Drugs 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 210000002345 respiratory system Anatomy 0.000 description 3
- 210000002460 smooth muscle Anatomy 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 210000000582 semen Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 102100033213 Teneurin-1 Human genes 0.000 description 1
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 229960000711 alprostadil Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940095074 cyclic amp Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 230000004882 diastolic arterial blood pressure Effects 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 230000003325 follicular Effects 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- SZINCDDYCOIOJQ-UHFFFAOYSA-L manganese(2+);octadecanoate Chemical compound [Mn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O SZINCDDYCOIOJQ-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000000754 myometrium Anatomy 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000004873 systolic arterial blood pressure Effects 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 108010063973 teneurin-1 Proteins 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000008673 vomiting Effects 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- 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
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
- C07C53/128—Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
-
- 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
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL49325A IL49325A (en) | 1976-03-31 | 1976-03-31 | 8-aza-11-deoxy-pge1 derivatives,their preparation and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL107544B1 true PL107544B1 (pl) | 1980-02-29 |
Family
ID=11048789
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977210101A PL107544B1 (pl) | 1976-03-31 | 1977-03-29 | Sposob wytwarzania nowych pochodnych prostaglandyn |
| PL1977197005A PL107643B1 (pl) | 1976-03-31 | 1977-03-29 | Sposob wytwarzania nowych pochodnych prostaglandyn |
| PL1977210102A PL108289B1 (pl) | 1976-03-31 | 1977-03-29 | Sposob wytwarzania nowych pochodnych prostaglandynmethod of producing new derivatives of prostaglandins |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977197005A PL107643B1 (pl) | 1976-03-31 | 1977-03-29 | Sposob wytwarzania nowych pochodnych prostaglandyn |
| PL1977210102A PL108289B1 (pl) | 1976-03-31 | 1977-03-29 | Sposob wytwarzania nowych pochodnych prostaglandynmethod of producing new derivatives of prostaglandins |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4115401A (Direct) |
| JP (1) | JPS52142060A (Direct) |
| BE (1) | BE852941A (Direct) |
| CA (1) | CA1074804A (Direct) |
| CH (2) | CH624101A5 (Direct) |
| DD (1) | DD130352A5 (Direct) |
| DE (1) | DE2714129A1 (Direct) |
| ES (1) | ES457385A1 (Direct) |
| FR (1) | FR2346332A1 (Direct) |
| GB (1) | GB1574246A (Direct) |
| HU (1) | HU178040B (Direct) |
| IL (1) | IL49325A (Direct) |
| IT (1) | IT1075373B (Direct) |
| NL (1) | NL7703503A (Direct) |
| NO (1) | NO149428C (Direct) |
| PL (3) | PL107544B1 (Direct) |
| SE (1) | SE417603B (Direct) |
| SU (3) | SU676162A3 (Direct) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU530907B2 (en) * | 1978-07-11 | 1983-08-04 | Glaxo Group Limited | Prostanoid compounds |
| US4320136A (en) * | 1980-08-11 | 1982-03-16 | E. I. Du Pont De Nemours And Company | 8-Aza-16,16-difluoroprostanoids |
| US4456613A (en) * | 1982-12-27 | 1984-06-26 | E. I. Du Pont De Nemours And Company | 6-Keto- and 6-hydroxy-8-azaprostanoids and anti-ulcer use thereof |
| US4530933A (en) * | 1982-12-27 | 1985-07-23 | E. I. Du Pont De Nemours And Company | 8-Aza-13-thiaprostanoids and a method of use thereof as anti-ulcer agents |
| AP2002002555A0 (en) | 1999-12-22 | 2002-06-30 | Pfizer Prod Inc | EP4 Receptor selective agonists in the treatment of osteoporosis. |
| DK1339678T3 (da) | 2000-11-27 | 2008-02-04 | Pfizer Prod Inc | Selektive agonister til EP4-receptor til behandling af osteoporose |
| CN100371322C (zh) * | 2001-07-16 | 2008-02-27 | 霍夫曼-拉罗奇有限公司 | 作为前列腺素类化合物激动剂的2-吡咯烷酮衍生物 |
| ATE315022T1 (de) | 2001-07-16 | 2006-02-15 | Hoffmann La Roche | Prostaglandinanaloga als ep4-rezeptoragonisten |
| BR0211364A (pt) | 2001-07-23 | 2004-07-13 | Ono Pharmaceutical Co | Composição farmacêutica para tratamento de doenças associadas com redução na massa óssea compreendendo o agonista ep4 como componente ativo |
| JP4547912B2 (ja) | 2002-03-05 | 2010-09-22 | 小野薬品工業株式会社 | ８−アザプロスタグランジン誘導体化合物およびその化合物を有効成分として含有する薬剤 |
| JP2005526080A (ja) * | 2002-03-18 | 2005-09-02 | ファイザー・プロダクツ・インク | 肝不全、動脈管閉鎖、緑内障又は高眼圧の治療のための選択的ｅｐ４受容体アゴニストの使用 |
| MXPA05007341A (es) * | 2003-01-10 | 2005-09-30 | Hoffmann La Roche | Derivados de 2-piperidona como agonistas de prostaglandina. |
| US7179820B2 (en) | 2003-06-06 | 2007-02-20 | Allergan, Inc. | Piperidinyl prostaglandin E analogs |
| US20080058375A1 (en) * | 2004-01-08 | 2008-03-06 | Elworthy Todd R | 2-Piperidone derivatives as prostaglandin antagonists |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3975399A (en) * | 1974-08-06 | 1976-08-17 | E. I. Du Pont De Nemours And Company | 1,5-Disubstituted-2-pyrrolidinones, -3-pyrrolin-2-ones, and -4-pyrrolin-2-ones |
-
1976
- 1976-03-31 IL IL49325A patent/IL49325A/xx unknown
-
1977
- 1977-03-28 BE BE176164A patent/BE852941A/xx not_active IP Right Cessation
- 1977-03-28 GB GB12991/77A patent/GB1574246A/en not_active Expired
- 1977-03-29 DD DD7700198124A patent/DD130352A5/xx unknown
- 1977-03-29 PL PL1977210101A patent/PL107544B1/pl unknown
- 1977-03-29 PL PL1977197005A patent/PL107643B1/pl unknown
- 1977-03-29 PL PL1977210102A patent/PL108289B1/pl unknown
- 1977-03-30 CA CA275,134A patent/CA1074804A/en not_active Expired
- 1977-03-30 NO NO771134A patent/NO149428C/no unknown
- 1977-03-30 SE SE7703698A patent/SE417603B/xx unknown
- 1977-03-30 DE DE19772714129 patent/DE2714129A1/de not_active Withdrawn
- 1977-03-30 CH CH400377A patent/CH624101A5/fr not_active IP Right Cessation
- 1977-03-30 HU HU77LA913A patent/HU178040B/hu unknown
- 1977-03-31 IT IT21906/77A patent/IT1075373B/it active
- 1977-03-31 FR FR7709650A patent/FR2346332A1/fr active Granted
- 1977-03-31 US US05/783,284 patent/US4115401A/en not_active Expired - Lifetime
- 1977-03-31 SU SU772465855A patent/SU676162A3/ru active
- 1977-03-31 JP JP3742877A patent/JPS52142060A/ja active Pending
- 1977-03-31 ES ES457385A patent/ES457385A1/es not_active Expired
- 1977-03-31 NL NL7703503A patent/NL7703503A/xx not_active Application Discontinuation
-
1978
- 1978-03-30 SU SU782594353A patent/SU837321A3/ru active
- 1978-03-30 SU SU782595450A patent/SU715019A3/ru active
-
1980
- 1980-09-17 CH CH697780A patent/CH628032A5/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL108289B1 (pl) | 1980-03-31 |
| CA1074804A (en) | 1980-04-01 |
| FR2346332A1 (fr) | 1977-10-28 |
| SU837321A3 (ru) | 1981-06-07 |
| NO771134L (no) | 1977-10-03 |
| DE2714129A1 (de) | 1977-10-13 |
| CH624101A5 (Direct) | 1981-07-15 |
| BE852941A (fr) | 1977-09-28 |
| IL49325A (en) | 1979-11-30 |
| SE7703698L (sv) | 1977-10-01 |
| SU715019A3 (ru) | 1980-02-05 |
| PL197005A1 (pl) | 1978-10-09 |
| ES457385A1 (es) | 1978-02-01 |
| US4115401A (en) | 1978-09-19 |
| PL107643B1 (pl) | 1980-02-29 |
| JPS52142060A (en) | 1977-11-26 |
| NO149428B (no) | 1984-01-09 |
| FR2346332B1 (Direct) | 1980-05-09 |
| IT1075373B (it) | 1985-04-22 |
| HU178040B (en) | 1982-02-28 |
| DD130352A5 (de) | 1978-03-22 |
| SU676162A3 (ru) | 1979-07-25 |
| NO149428C (no) | 1984-04-18 |
| NL7703503A (nl) | 1977-10-04 |
| SE417603B (sv) | 1981-03-30 |
| IL49325A0 (en) | 1976-05-31 |
| CH628032A5 (fr) | 1982-02-15 |
| GB1574246A (en) | 1980-09-03 |
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