FI105106B - Förfarande för framställning av optiskt aktiv (2S)-endo-bicyklo[2.2.1]heptan-2-ol eller (2R)-endo-bicyklo[2.2.1]heptan-2-ol och vid förfarandet användbara mellanprodukter - Google Patents
Förfarande för framställning av optiskt aktiv (2S)-endo-bicyklo[2.2.1]heptan-2-ol eller (2R)-endo-bicyklo[2.2.1]heptan-2-ol och vid förfarandet användbara mellanprodukter Download PDFInfo
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- FI105106B FI105106B FI922142A FI922142A FI105106B FI 105106 B FI105106 B FI 105106B FI 922142 A FI922142 A FI 922142A FI 922142 A FI922142 A FI 922142A FI 105106 B FI105106 B FI 105106B
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- bicyclo
- exo
- heptan
- yloxy
- hept
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
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- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Dermatology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Claims (13)
1. Förfarande för framställning av optiskt aktiv (2S)-endo-bicyklo [2.2.1]heptan-2-ol eller (2R)-endo-bicy- 5 klo[2.2.1]heptan-2-ol, kännetecknat av att det omfattar steg, väri: (a) en partiell transförestring mellan racemisk endo-bicyklo[2.2.1]heptan-2-ol och 2,2,2-trikloretylbuty-rat utförs i ett väsentligen vattenfritt, reaktionsinert 10 organiskt lösningsmedel i närvaro av en katalytisk mängd av ett däggdjurs bukspottkörtellipas för att bilda en blandning, som innehäller nämnda (2S)-endo-bicyklo [2 . 2 . 1] heptan-2 -oi och smörsyraester av (2R)-endo-bicy-lo[2.2.1]heptan-2-oi; och 15 (b) nämnda (2S)-endo-bicyklo[2.2.1]heptan-2-oi se- pareras frän nämnda blandning; eller nämnda smörsyraester av (2R)-endo-bicyklo [2 . 2 . 1] heptan-2-ol separeras frän nämnda blandning, och hydrolyseras pä konventionellt sätt för framställning av 20 nämnda (2R)-endo-bicyklo[2.2.1]heptan-2-ol.
2. Förfarande enligt patentkrav 1 för framställning av (2S)-endo-bicyklo[2.2.1]heptan-2-oi.
3. Förfarande enligt patentkrav 1 för framställning av (2R)-endo-bicyklo[2.2.1]heptan-2-oi. 25
4. Förfarande enligt patentkrav 2, k ä n n e - kännetecknat av att lipaset härstammar frän svin.
5. Förfarande enligt patentkrav 3, kännetecknat av att lipaset härstammar frän svin. 30
6. Förfarande enligt patentkrav 4, kanne- . : tecknatav att det reaktionsinerta lösningsmedlet är eter.
7. Förfarande enligt patentkrav 5, kännetecknat av att det reaktionsinerta lösningsmedlet 35 är eter. • 24 705706
8. Förfarande enligt patentkrav 1, kanne-tecknat av att det ytterligare omfattar omvandling av nämnda (2S)-endo-bicyklo[2.2.1]heptan-2-oi eller (2R) -endo-bicyklo[2.2.1]heptan-2-oi pä motsvarande sätt tili 5-5 (3 -[(2R)-exo-bicyklo[2.2.1]hept-2-yloxi]-4-metoxifenyl)- 3,4,5,6-tetrahydropyrimidin-2(1H)-on eller 5-(3-[(2S)-exo-bicyklo [2.2.1]hept-2-yloxi]-4-metoxifenyl)-3,4,5,6-tetra-hydropyrimidin-2(1H)-on med steg, väri: (c) nämnda (2S)-endo-bicyklo[2.2.1]heptan-2-oi eliö ler (2R)-endo-bicyklo[2.2.1]heptan-2-ol fäs att reagera med ätminstone 1 molekvivalent av 3-hydroxi-4-metoxi-ben-saldehyd väsentligen i närvaro av 1 molekvivalent av säväl trifenylfosfin som dietylazodikarboxylat i ett reaktion-sinert lösningsmedel vid en temperatur inom omrädet ca 50 15 - 100 °C för att bilda 3-[ (2R)-exo-bicyklo[2.2.1]hept-2- yloxi]-4-metoxibensaldehyd eller 3-[(2S)-exo-bicyklo [2.2.1] hept-2-yloxi]-4-metoxibensaldehyd; (d) nämnda 3-[(2R)-exo-bicyklo[2.2.1]hept-2-yloxi]- 4-metoxibensaldehyd eller 3-[(2S)-exo-bicyklo[2.2.1]hept- 20 2-yloxi]4-metoxibensaldehyd fäs att reagera med ätminstone tvä molekvivalenter av 2-cyanättiksyra i pyridin i närvaro av en katalytisk mängd piperidin vid en temperatur inom omrädet ca 25 - 100 °C för att bilda 3-(3-[(2R)-exo-bicyklo [2 . 2 .1] hept-2-yloxi ]-4-metoxif enyl) pentandinitril el-25 ler 3-(3-[(2S)-exo-bicyklo[2.2.1]hept-2-yloxi]-4-metoxi- fenyl) pentandinitril; (e) nämnda 3 -(3 -[(2R)-exo-bicyklo[2.2.1]hept-2-yloxi]-4-metoxif enyl) pentandinitril eller 3 - (3-[ (2S)-exo-bicyklo [2.2.1]hept-2-yloxi]-4-metoxifenyl) pentandinitril 30 hydratiseras pä konventionellt sätt för att bilda 3-(3- : [(2R)-exo-bicyklo[2.2.1]hept-2-yloxi]-4-metoxifenyl) gluta- ramid eller 3-(3-[(2S)-exo-bicyklo[2.2.1]hept-2-yloxi]-4-metoxifenyl)glutaramid; och (f) nämnda 3-(3-[(2R)-exo-bicyklo[2.2.1]hept-2-ylo- 35 xi]-4-metoxifenyl) glutaramid eller 3-(3-[(2S)-exo-bicy- t 25 1°5106 klo[2.2.1]hept-2-yloxi]-4-metoxifenyl)glutaramid cyk- liseras i närvaro av ett moloverskott av blytetraacetat i pyridin för att bilda narnnda 5-(3- [ (2R)-exo-bicy-klo[2.2.1]hept-2-yloxi]-4-metoxifenyl)-3,4,5,6- tetrahyd-5 ropyrimidin-2(1H)-on eller 5- (3 - [ (2S) -exo-bicy- klo[2.2.1]hept-2-yloxi]-4-metoxifenyl)-3,4,5,6-tetrahydro-pyrimidin-2(1H)-on.
9. Förfarande enligt patentkrav 8, kanne-tecknat av att (2S)-endo-bicyklo[2.2.1]heptan-2-ol 10 omvandlas till 5-(3-[(2R)-exo-bicyklo[2.2.1]hept-2-yloxi]- 4-metoxifenyl)-3,4,5,6- tetrahydropyrimidin-2(1H)-on.
10. Förfarande enligt patentkrav 8, kanne-tecknat av att (2R)-endo-bicyklo[2.2.1]heptan-2-ol omvandlas till 5-(3-[ (2S)-exo-bicyklo[2.2.1] hept-2-ylo- 15 xi]-4-metoxifenyl)-3,4,5,6- tetrahydropyrimidin-2(1H)-on.
11. Optiskt aktiv förening, kanne -tecknad av att den valts frän gruppen bestciende av en förening med den absoluta stereokemiska formeln V
20 OCH, . y y och en förening med den absoluta stereokemiska formeln VI 26 1 05 1 06 A\ o^C3 Λ Υ Υ ίο väri Υ är -CN eller -CONH2.
12. Förening enligt patentkrav 11, kanne-t e c k n a d av att Y är -CN.
13. Förening enligt patentkrav 11, kanne- 15 tecknad av att Y är -C0NH2. «
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8905228 | 1989-11-13 | ||
| PCT/US1989/005228 WO1991007501A1 (en) | 1989-11-13 | 1989-11-13 | Enzymatic resolution of endo-bicyclo[2.2.1]heptan-2-ol and derived pharmaceutical agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI922142A FI922142A (fi) | 1992-05-12 |
| FI922142A0 FI922142A0 (fi) | 1992-05-12 |
| FI105106B true FI105106B (sv) | 2000-06-15 |
Family
ID=22215375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI922142A FI105106B (sv) | 1989-11-13 | 1992-05-12 | Förfarande för framställning av optiskt aktiv (2S)-endo-bicyklo[2.2.1]heptan-2-ol eller (2R)-endo-bicyklo[2.2.1]heptan-2-ol och vid förfarandet användbara mellanprodukter |
Country Status (27)
| Country | Link |
|---|---|
| EP (2) | EP0428302B1 (sv) |
| JP (1) | JPH06104661B2 (sv) |
| KR (1) | KR930004654B1 (sv) |
| CN (1) | CN1040423C (sv) |
| AT (1) | ATE158577T1 (sv) |
| AU (3) | AU633157B2 (sv) |
| CA (1) | CA2029705C (sv) |
| CZ (2) | CZ280006B6 (sv) |
| DE (1) | DE69031487T2 (sv) |
| DK (1) | DK0428302T3 (sv) |
| EG (1) | EG19860A (sv) |
| ES (1) | ES2107420T3 (sv) |
| FI (1) | FI105106B (sv) |
| GR (1) | GR3025196T3 (sv) |
| HU (2) | HU215441B (sv) |
| IE (2) | IE904059A1 (sv) |
| IL (5) | IL110568A (sv) |
| MY (1) | MY104517A (sv) |
| NO (1) | NO304838B1 (sv) |
| NZ (1) | NZ236037A (sv) |
| PH (1) | PH30255A (sv) |
| PL (4) | PL165132B1 (sv) |
| PT (1) | PT95855B (sv) |
| RU (1) | RU2104306C1 (sv) |
| WO (1) | WO1991007501A1 (sv) |
| YU (1) | YU48413B (sv) |
| ZA (1) | ZA909044B (sv) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU215441B (hu) * | 1989-11-13 | 1999-04-28 | Pfizer Inc. | Eljárás az endo-biciklo [2.2.1]-heptan-2-ol előállítására és az ebből kapott hatóanyagok enzimatikus úton történő elválasztására |
| US5124455A (en) * | 1990-08-08 | 1992-06-23 | American Home Products Corporation | Oxime-carbamates and oxime-carbonates as bronchodilators and anti-inflammatory agents |
| IE71647B1 (en) | 1991-01-28 | 1997-02-26 | Rhone Poulenc Rorer Ltd | Benzamide derivatives |
| NZ246087A (en) * | 1991-12-06 | 1995-04-27 | Shionogi Seiyaku Kk | Production of optically active norborneol from a racemic ester mixture using a microoganism or treated cells thereof |
| US5814651A (en) * | 1992-12-02 | 1998-09-29 | Pfizer Inc. | Catechol diethers as selective PDEIV inhibitors |
| BR9307570A (pt) * | 1992-12-02 | 1999-05-25 | Pfizer | Diéteres de catecol como inibidores seletivos de pdeiv |
| JP3431204B2 (ja) * | 1993-04-22 | 2003-07-28 | 塩野義製薬株式会社 | ノルボルナン型エステル・ヒドロラーゼ |
| CN1041436C (zh) * | 1993-05-07 | 1998-12-30 | 佛山市制药一厂 | 一种稳定冯了性风湿跌打药酒的方法 |
| US5482944A (en) * | 1993-07-13 | 1996-01-09 | Pfizer Inc. | Pyrimidones and imidazolinones for treatment of shock |
| JPH1142095A (ja) * | 1997-07-25 | 1999-02-16 | Chisso Corp | 新規なオキソジシクロペンタジエンの製造方法 |
| KR100479019B1 (ko) * | 1998-05-22 | 2005-08-29 | 씨제이 주식회사 | 캐테콜히드라존유도체,이의제조방법및그를함유한약제학적조성물 |
| MXPA02001830A (es) | 1999-08-21 | 2002-08-12 | Byk Gulden Lomberg Chem Fab | Combinacion sinergica de inhibidores de pde y agonista de beta 2 adrenoceptor. |
| WO2003002511A1 (fr) | 2001-06-29 | 2003-01-09 | Nikken Chemicals Co., Ltd. | Derive de cycloalcenone |
| ES2194588B1 (es) * | 2001-07-13 | 2004-10-16 | Astur Pharma S.A. | Precursores opticamente puros de paroxetina. |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| EA200501548A1 (ru) | 2003-04-01 | 2006-02-24 | Апплайд Резеч Системз Арс Холдинг Н.В. | Ингибиторы фосфодиэстераз при бесплодии |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| DK2170930T3 (da) | 2007-06-04 | 2012-11-05 | Synergy Pharmaceuticals Inc | Agonister af guanylatcyclase, anvendelige til behandlingen af gastrointestinale sygdomme, inflammation, cancer og andre sygdomme |
| JP2011522828A (ja) | 2008-06-04 | 2011-08-04 | シナジー ファーマシューティカルズ インコーポレイテッド | 胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| ES2664873T3 (es) | 2011-03-01 | 2018-04-23 | Synergy Pharmaceuticals Inc. | Proceso de preparación de agonistas de guanilato ciclasa C |
| EP2958577A2 (en) | 2013-02-25 | 2015-12-30 | Synergy Pharmaceuticals Inc. | Guanylate cyclase receptor agonists for use in colonic cleansing |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| KR102272746B1 (ko) | 2013-06-05 | 2021-07-08 | 보슈 헬스 아일랜드 리미티드 | 구아닐레이트 사이클라제 c의 초순수 작용제, 및 이의 제조 및 사용 방법 |
| KR20220147691A (ko) | 2013-08-09 | 2022-11-03 | 알데릭스, 인코포레이티드 | 인산염 수송을 억제하기 위한 화합물 및 방법 |
| JP2022533251A (ja) | 2019-05-21 | 2022-07-21 | アルデリックス， インコーポレイテッド | 患者において血清リン酸塩を低下させるための組み合わせ |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4261995A (en) * | 1979-08-31 | 1981-04-14 | Syntex (U.S.A.) Inc. | 4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydropyrimidine derivatives |
| US4732853A (en) * | 1984-11-21 | 1988-03-22 | President And Fellows Of Harvard College | Method of making chiral epoxy alcohols |
| WO1987006576A1 (en) * | 1986-04-29 | 1987-11-05 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
| HU215441B (hu) * | 1989-11-13 | 1999-04-28 | Pfizer Inc. | Eljárás az endo-biciklo [2.2.1]-heptan-2-ol előállítására és az ebből kapott hatóanyagok enzimatikus úton történő elválasztására |
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1989
- 1989-11-13 HU HUP9201587A patent/HU215441B/hu not_active IP Right Cessation
- 1989-11-13 CZ CS921240A patent/CZ280006B6/cs not_active IP Right Cessation
- 1989-11-13 RU SU5052372A patent/RU2104306C1/ru not_active IP Right Cessation
- 1989-11-13 HU HU9802988A patent/HU220962B1/hu not_active IP Right Cessation
- 1989-11-13 WO PCT/US1989/005228 patent/WO1991007501A1/en active IP Right Grant
-
1990
- 1990-11-02 ES ES90312019T patent/ES2107420T3/es not_active Expired - Lifetime
- 1990-11-02 DK DK90312019.4T patent/DK0428302T3/da active
- 1990-11-02 AT AT90312019T patent/ATE158577T1/de not_active IP Right Cessation
- 1990-11-02 EP EP90312019A patent/EP0428302B1/en not_active Expired - Lifetime
- 1990-11-02 EP EP97103886A patent/EP0801135A1/en not_active Ceased
- 1990-11-02 DE DE69031487T patent/DE69031487T2/de not_active Expired - Fee Related
- 1990-11-06 IL IL11056890A patent/IL110568A/en active IP Right Grant
- 1990-11-06 IL IL9626190A patent/IL96261A/en active IP Right Grant
- 1990-11-06 IL IL110564A patent/IL110564A/en active IP Right Grant
- 1990-11-09 CA CA002029705A patent/CA2029705C/en not_active Expired - Fee Related
- 1990-11-11 EG EG67090A patent/EG19860A/xx active
- 1990-11-12 YU YU214290A patent/YU48413B/sh unknown
- 1990-11-12 IE IE405990A patent/IE904059A1/en not_active IP Right Cessation
- 1990-11-12 KR KR1019900018244A patent/KR930004654B1/ko not_active IP Right Cessation
- 1990-11-12 PT PT95855A patent/PT95855B/pt not_active IP Right Cessation
- 1990-11-12 PL PL90301764A patent/PL165132B1/pl unknown
- 1990-11-12 CN CN90109076A patent/CN1040423C/zh not_active Expired - Fee Related
- 1990-11-12 MY MYPI90001992A patent/MY104517A/en unknown
- 1990-11-12 NZ NZ236037A patent/NZ236037A/en unknown
- 1990-11-12 AU AU66535/90A patent/AU633157B2/en not_active Ceased
- 1990-11-12 IE IE19980174A patent/IE980174A1/en not_active IP Right Cessation
- 1990-11-12 ZA ZA909044A patent/ZA909044B/xx unknown
- 1990-11-12 PL PL90292070A patent/PL164457B1/pl unknown
- 1990-11-12 PL PL90292069A patent/PL164202B1/pl unknown
- 1990-11-12 PL PL90287727A patent/PL164176B1/pl unknown
- 1990-11-13 JP JP2306942A patent/JPH06104661B2/ja not_active Expired - Fee Related
- 1990-11-13 CZ CS905609A patent/CZ280011B6/cs not_active IP Right Cessation
-
1992
- 1992-05-12 FI FI922142A patent/FI105106B/sv not_active IP Right Cessation
- 1992-05-12 NO NO921876A patent/NO304838B1/no unknown
-
1993
- 1993-01-22 AU AU31979/93A patent/AU645449B2/en not_active Ceased
- 1993-02-09 AU AU32920/93A patent/AU3292093A/en not_active Withdrawn
- 1993-10-12 PH PH47065A patent/PH30255A/en unknown
-
1994
- 1994-08-04 IL IL11056494A patent/IL110564A0/xx unknown
- 1994-08-04 IL IL11056894A patent/IL110568A0/xx unknown
-
1997
- 1997-10-29 GR GR970402831T patent/GR3025196T3/el unknown
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| MA | Patent expired |